Mmp-13 selective inhibitor

ABSTRACT

Since it is thought that if the activity of MMP-13 can be inhibited, this will largely contribute to improvement or prevention of progession of pathological states, particularly, osteoarthritis (OA), resulting from or associated with the MMP-13 activity, the development of MMP-13 inhibitors is anticipated. There are provided a compound represented by the general formula (I): 
     
       
         
         
             
             
         
       
     
     wherein R 1  is optionally substituted aryl etc.; Z is C1-C5 alkylene which may be substituted and may be interrupted with a substituent selected from Substituent group a etc.; A is the formula: 
     
       
         
         
             
             
         
       
     
     (R 6  and R 7  are each independently halogen, lower alkyl etc.; m and n are each independently 0, 1, or 2); R 2  is a hydrogen atom, optionally substituted lower alkyl etc.; R 3  is a hydrogen atom, optionally substituted lower alkyl etc.; R 4  is a hydrogen atom; or R 3  and R 4  may be taken together with an adjacent carbon atom to from a ring; R 5  is hydroxy, lower alkyloxy etc.), or an optically active isomer, a pharmaceutically acceptable salt or a solvate thereof, and a pharmaceutical composition containing it as an active ingredient, which has the MMP-13 inhibiting activity.

TECHNICAL FIELD

The present invention relates to sulfonamide derivatives whichselectively inhibit MMP-13.

BACKGROUND TECHNIQUE

An extracellular matrix is composed of collagen, fibronectin, laminine,proteoglycan and the like, and has a role of tissue supporting function,proliferation, differentiation and adhesion of cells, and the like.Degradation of an extracellular matrix is associated withmetalloprotease which is a protease containing a metal ion in an activecenter, particularly, matrix metalloprotease (MMP). As for the MMPfamily, many members were reported from MMP-1 (I type collagenase) toMMP-28, and they act on growth, tissue metabolism and the like under theoriginal physiological conditions. However, it was reported that theprogress were correlated with the increase in expression (activity) ofthe above enzymes in various pathological states which were accompaniedby the destruction of tissues and fibrosis (osteoarthritis, articularrheumatism, corneal ulcer, periodontic disease, metastasis orinfiltration of tumor, virus infectious disease (HIV infectiousdisease)).

The sulfonamide derivatives having MMP inhibiting activities weredescribed in Patent Literature 1, Patent Literature 2, Patent Literature3 and Non-Patent Literature 1.

The sulfonamide derivatives having MMP-12 inhibiting activity, andhaving a naphthyl group as a substituent were described in PatentLiterature 4.

The thiazoles or oxazolesulfonamide derivatives having a naphtyl groupas a substituent were described in Patent Literature 5.

The thiazoles or oxazolesulfonamide derivatives having a naphtyl groupas a substituent were described in Patent Literature 6.

The sulfonamide derivatives having aglycanase inhibiting activity, andhaving a naphtyl group as a substituent were described in PatentLiterature 7.

The sulfonamide derivatives having aggrecanase inhibiting activity andMMP-13 inhibiting activity were described in Patent Literature 8.

The sulfonamide derivatives having aggrecanase inhibiting activity andMMP inhibiting activities were described in Patent Literature 9.

The sulfonamide derivatives having TNF-α inhibiting activity and the MMPinhibiting activities were described in Patent Literature 10.

[Patent Literature 1] International Publication WO 97/27174

[Patent Literature 2] International Publication WO 99/04780

[Patent Literature 3] International Publication WO 00/15213

[Patent Literature 4] International Publication WO 01/83431

[Patent Literature 5 International Publication WO 02/28844

[Patent Literature 6] International Publication WO 01/83461

[Patent Literature 7] International Publication WO 03/080042

[Patent Literature 8] Japanese Patent Application Laid-Open (JP-A)

[Patent Literature 9] International Publication WO 05/061459

[Patent Literature 10] International Publication WO 98/32748

[Non-Patent Literature 1] Yoshinori Tamura et al., J. Med. Chem., 1998,vol. 41, No. 4, p. 640-649

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

Since it is thought that if the activity of MMP-13 can be inhibited,this will contribute to improvement or prevention of progession ofpathological states, particularly, osteoarthritis (OA), resulting fromor associated with the MMP-13 activity, the development of MMP-13inhibitors is anticipated.

Means to Solve the Problems

In view of the aforementioned respects, the present inventorsintensively continued to study and they completed the followinginvention by finding that some novel sulfonamide derivatives exhibit theMMP-13 selective inhibiting activity.

The present invention relates to: 1) a compound represented by thegeneral formula (I):

wherein R¹ is optionally substituted aryl, optionally substitutedheteroaryl, an optionally substituted non-aromatic carbocyclic group, oran optionally substituted non-aromatic heterocyclic group;Z is —O—, —S—, —SO—, —SO₂—, —N(R¹⁰)—, —N(R¹⁰)—C(═O)—, —C(═O)—N(R¹⁰)—,—N(R¹⁰)—SO₂—, —SO₂—N(R¹⁰)—, —C(═O)—, —O—C(═O)—, —C(═O)—O—,—N(R¹⁰)—C(═O)—N(R¹⁰)—, —N(R¹⁰), —C(═S)—N(R¹⁰)—, —O—N═C(R⁸)—,—C(R⁸)═N—O—, —O—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═O)—O—, —C(═O)C(═O)—, anoptionally substituted non-aromatic carbocyclic group, an optionallysubstituted non-aromatic heterocyclic group, C1-C5 alkylene which isoptionally substituted and may be intervened a substituent selected fromSubstituent group a, or C1-C5 alkenylene which is optionally substitutedand may be intervened with a substituent selected from Substituent groupa, or C1-C5 alkynylene which is optionally substituted and may beintervened with a substituent selected from Substituent group a, whereinthe Substituent group a consists of —O—, —S—, —SO—, —SO₂—, —N(R¹⁰)—,—N(R¹⁰)—C(═O)—, —C(═O)—N(R¹⁰)—, —N(R¹⁰)—SO₂—, —SO₂—N(R¹⁰)—, —C(═O)—,—O—C(═O)—, —C(═O)—O—, —N(R¹⁰)—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═S)—N(R¹⁰)—,—O—N═C(R⁸)—, —C(R⁸)═N—O—, —O—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═O)—O—, and—C(═O)—C(═O)—,R⁸ and R¹⁰ are each independently a hydrogen atom or lower alkyl;A is a group represented by the formula;

wherein R⁶ and R⁷ are each independently halogen, lower alkyl,cycloalkyl, lower alkenyl, lower alkynyl, lower alkyloxy, loweralkenyloxy, lower alkylthio, halo lower alkyl, halo lower alkyloxy, halolower alkylthio, hydroxy, hydroxy lower alkyl, mercapto, carboxy, loweralkyloxycarbonyl, lower alkylsulfonyl, acyl, acyloxy, nitro, cyano,optionally substituted amino, or optionally substituted aminocarbonyl;B ring is a nitrogen-containing heterocycle optionally furthercontaining a nitrogen atom, an oxygen atom, and/or a sulfur atom in thering;m and n are each independently an integer of 0 to 3;R² is a hydrogen atom, optionally substituted lower alkyl, optionallysubstituted aralkyl, optionally substituted heteroarylalkyl, optionallysubstituted aryl, or optionally substituted heteroaryl;R³ is a hydrogen atom, optionally substituted lower alkyl, optionallysubstituted aralkyl, optionally substituted heteroarylalkyl, optionallysubstituted aryl, or optionally substituted heteroaryl;R⁴ is a hydrogen atom, orR³ and R⁴ may be taken together with an adjacent carbon atom to form a 5to 6-membered non-aromatic carbocyclic ring or a 5- to 6-memberednon-aromatic heterocyclic ring;R⁵ is hydroxy, lower alkyloxy, or —NHOH;provided that when B ring is piperazine, and Z is —CH₂—O—, R¹ is notpyridyl an optically active isomer, a pharmaceutically acceptable saltor a solvate thereof.

More particularly, the present invention relates to the following 2) to27).

2) The compound according to 1), which is represented by the generalformula (II):

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Z, m, n and B ring are as defined in1), an optically active isomer, a pharmaceutically acceptable salt or asolvate thereof.3) The compound according to 1), which is represented by the generalformula (III):

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Z, m, n and B ring are as defined in1), an optically active isomer, a pharmaceutically acceptable salt or asolvate thereof.4) The compound according to any one of 1) to 3), wherein R¹ isoptionally substituted naphthyl or optionally substituted carbazolyl, anoptically active isomer, a pharmaceutically acceptable salt or a solvatethereof.5) The compound according to any one of 1) to 3), wherein R¹ isoptionally substituted naphthyl, or an optically active isomer, apharmaceutically acceptable salt or a solvate thereof.6) The compound according to 5), wherein R¹ is a group represented bythe formula:

wherein R²⁴ is a hydrogen atom; lower alkyl optionally substituted withcarboxy or lower alkyloxyimino; lower alkenyl optionally substitutedwith carboxy; hydroxy; lower alkyloxy optionally substituted withcycloalkyl, hydroxy, lower alkyloxy, carboxy, or aminocarbonyloptionally substituted with 1 or 2 lower alkyl(s); carboxy; acyl; aminooptionally substitute with 1 or 2 acyl(s) or lower alkylsulfonyl(s);aminocarbonyl optionally substituted with 1 or 2 lower alkyl(s); or anon-aromatic heterocycle;R²⁵ is halogen, cyano, or acyl;n¹ is an integer of 0 to 2, and R²⁵ may be substituted on allreplaceable constituent carbon atoms, an optically active isomer, apharmaceutically acceptable salt, or a solvate thereof. Among theabovementioned compounds, the compounds in which n¹ is 0 are preferable.7) The compound according to 5), wherein R¹ is a group represented bythe formula:

wherein R²⁴, R²⁵, and n¹ are as defined in 6,);an optically active isomer, a pharmaceutically acceptable salt or asolvate thereof. Among the abovementioned compounds, the compounds inwhich n¹ is 0 are preferable.8) The compound according to 5), wherein R¹ is a group represented bythe formula:

wherein R²⁴, R²⁵, and n¹ are as defined in 6);an optically active isomer, a pharmaceutically acceptable salt or asolvate thereof. Among the abovementioned compounds, the compounds inwhich n¹ is 0 are preferable.9) The compound according to any one of 6) to 8), wherein R²⁴ is ahydrogen atom, lower alkyloxy, or amino, or an optically active isomer,a pharmaceutically acceptable salt or a solvate thereof.10) The compound according to any one of 1) to 3), wherein R¹ isoptionally substituted carbazolyl, or an optically active isomer, apharmaceutically acceptable salt or a solvate thereof. Among theabovementioned compounds, the compounds in which R¹ is unsubstitutedcarbazolyl are preferable.11) The compound according to any one of 1) to 10), wherein Z is—C(R⁸)(R⁹)—, —O—, S—, —SO—, —SO₂—, —N(R¹⁰)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—,—C(R⁸)═C(R⁹)—, —C≡C—, —O—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—O—, —S—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—S—, —SO—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO—, —SO₂—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—SO₂—, —N(R¹⁰)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—N(R¹⁰)—, —N(R¹⁰)—C(═O)—,—C(═O)—N(R¹⁰)—, —N(R¹¹)—SO₂—, —SO₂—N(R¹⁰)—, —C(R⁸)(R⁹)—C(═O)—,—C(═O)—C(R⁸)(R⁹)—, —C(═O)C(═O)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—C(R⁸)═C(R⁹)—, —C(R⁸)═C(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C≡C—,—C≡C—C(R⁸)(R⁹)—, —O—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—O—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—O—, —S—C(R⁸)(R⁹)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—S—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—S—,—SO—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—SO—, —SO₂—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—SO₂—, —N(R¹⁰)—C(R⁸)(R⁹)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—N(R¹⁰)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—N(R¹⁰)—,—C(═O)—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(═O)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—C(═O)—, —C(R⁸)(R⁹)—N(R¹⁰)—C(═O)—,—N(R¹⁰)—C(═O)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(═O)—N(R¹⁰)—,—C(═O)—N(R¹⁰)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—N(R¹⁰)—SO₂—,—N(R¹⁰)—SO₂—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—N(R¹⁰)—, —SO₂—N(R¹⁰)—C(R⁸)(R⁹)—,—N(R¹⁰)—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═S)—N(R¹⁰)—, —O—N═C(R⁸)—, —C(R⁸)═N—O—,—O—C(═O)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(═O)—O—, —O—C(═O)—N(R¹⁰)—, or—N(R¹⁰)—C(═O)—O—, wherein R⁸, R⁹ and R¹⁰ are each independently ahydrogen atom or lower alkyl, an optically active isomer, apharmaceutically acceptable salt or a solvate thereof.12) The compound according to any one of 1) to 10), wherein Z is—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)═C(R⁹)—, —C≡C—, —O—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—O—, —S—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—S—, —SO—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—SO—, —SO₂—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—, —N(R¹⁰)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—N(R¹⁰)—, —N(R¹⁰)—C(═O)—, —C(═O)—N(R¹⁰)—, —N(R¹⁰)—SO₂—,—SO₂—N(R¹⁰)—, —C(R⁸)(R⁹)—C(═O)—, —C(═O)—C(R⁸)(R⁹)—, or —C(═O)C(═O)—,wherein R⁸, R⁹ and R¹⁰ are each independently a hydrogen atom or loweralkyl, an optically active isomer, a pharmaceutically acceptable salt ora solvate thereof.13) The compound according to any one of 1) to 10), wherein Z is—CH₂—CH₂—, —CH═CH—, —C≡C—, —O—CH₂—, or —CH₂—O—, an optically activeisomer, a pharmaceutically acceptable salt or a solvate thereof.14) The compound according to any one of 1) to 10), wherein Z is —C≡C—,an optically active isomer, a pharmaceutically acceptable salt or asolvate thereof.15) The compound according to any one of 1) to 14), wherein a grouprepresented by the formula:

is a group represented by the formula:

wherein X is a carbon atom or a nitrogen atom, a C ring is a 5- to8-membered nitrogen-containing heterocycle, and R⁷ and m are as definedin 1), an optically active isomer, a pharmaceutically acceptable salt ora solvate thereof.16) The compound according to any one of 1) to 14), wherein a grouprepresented by the formula:

is a group represented by the formula:

wherein R⁷ and m are as defined in 1), an optically active isomer, apharmaceutically acceptable salt or a solvate thereof.17) The compound according to any one of 1) to 16), wherein R² is ahydrogen atom, or an optically active isomer, a pharmaceuticallyacceptable salt or a solvate thereof.18) The compound according to any one of 1) to 17), wherein R³ is ahydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl,isobutyl, t-butyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl,carboxymethyl, carboxyethyl, methyloxymethyl, methylthiomethyl,2-methylthioethyl, phenyl, 4-hydroxyphenyl, 4-fluorophenyl,4-methyloxyphenyl, benzyl, 4-hydroxybenzyl, 4-fluorobenzyl,4-chlorobenzyl, 4-methoxybenzyl, indol-3-ylmethyl,1-carboxymethylindol-3-ylmethyl, thiazol-4-ylmethyl,carboxymethyloxybenzyl, or cyclopropylmethyl;R⁴ is a hydrogen atom; orR³ and R⁴ may be taken together with an adjacent carbon to form a ringrepresented by the formula:

an optically active isomer, a pharmaceutically acceptable salt or asolvate thereof.19) The compound according to any one of 1) to 17), wherein R³ is ahydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl,isobutyl, t-butyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl,carboxymethyl, carboxyethyl, methyloxymethyl, methylthiomethyl,2-methylthioethyl, phenyl, 4-hydroxyphenyl, 4-fluorophenyl,4-methyloxyphenyl, benzyl, 4-hydroxybenzyl, 4-fluorobenzyl,4-chlorobenzyl, 4-methoxybenzyl, indol-3-ylmethyl,1-carboxymethylindol-3-ylmethyl, thiazol-4-ylmethyl,carboxymethyloxybenzyl, or cyclopropylmethyl, andR⁴ is a hydrogen atom, an optically active isomer, a pharmaceuticallyacceptable salt or a solvate thereof.20) The compound according to any one of 1) to 19), wherein R⁵ ishydroxy, an optically active isomer, a pharmaceutically acceptable saltor a solvate thereof.21) A pharmaceutical composition containing the compound as defined inany one of 1) to 20) as an active ingredient.22) A pharmaceutical composition for inhibiting MMP-13 which containsthe compound as defined in any one of 1) to 20) as an active ingredient.23) An agent for treating or preventing osteoarthritis containing thecompound as defined in any one of 1) to 20) as an active ingredient.24) A method of treating a disease resulting from, or associated withMMP-13 of a mammal, comprising administering an amount for exhibitingthe therapeutic effect of the compound as defined in any one of 1) to20) to a mammal including a human.25) A method of treating osteoarthritis of a mammal, comprisingadministering an amount for exhibiting the therapeutic effect of thecompound as defined in any one of 1) to 20) to a mammal including ahuman.26) Use of the compound as defined in any one of 1) to 20), forpreparing a medicament for treating a disease resulting from associatedwith MMP-13.27) Use of the compound as defined in any one of 1) to 20), forpreparing a medicament for treating osteoarthritis.

Herein, a term “lower alkyl” which is used alone or in combination withother terms includes linear or branched monovalent hydrocarbon groupscomprised of 1 to 8 carbon atoms. For example, they are methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl,isopentyl, neo-pentyl, n-hexyl, isohexyl, n-heptyl, n-octyl and thelike. Preferable examples are C1-C6 alkyls. Further preferable examplesare C1-C3 alkyls.

Herein, the “cycloalkyl” includes cycloalkyls comprised of 3 to 8 carbonatoms. For example they are cyclopropyl, cylobutyl, cyclopentyl,cyclohexyl, cycloheptyl and cyclooctyl. Preferable examples are C3-C6cycloalkyls.

Herein, the “lower alkenyl” which is used alone or in combination withother terms includes linear or branched monovalent hydrocarbon groupscomprised of 2 to 8 carbon atoms, having one or more double bonds. Forexample, they are vinyl, allyl, propenyl, crotonyl, isopentenyl, variousbutenyl isomers and the like. Preferable examples are C2-C6 alkenyls.Further preferable examples are C2-C4 alkenyls.

Herein, the “cycloalkenyl” includes cycloalkenyls comprised of 3 to 8carbon atoms, having one or more double bonds in the ring. For example,they are cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl,cycloheptenyl, and cyclooctenyl. Preferable examples are C3-C6cycloalkenyls.

Herein, the “lower alkynyl” includes linear or branched monovalenthydrocarbon groups comprised of 2 to 8 carbon atoms, having one or moretriple bonds, which may have a double bond. For example, they areethynyl, 2-propynyl, 3-butynyl, 4-pentynyl, 5-hexynyl, 6-heptynyl,7-octynyl and the like. Preferable examples are C2-C6 alkynyls. Furtherpreferable examples are C2-C4 alkynyls.

Herein, the “cycloalkynyl” includes cycloalkynyls comprised of 4 to 8carbon atoms, having one or more triple bonds in the ring, which mayhave a double bond. For example, they are cyclobutynyl, cyclopentynyl,cyclohexynyl, cycloheptynyl, and cyclooctynyl. Preferable examples areC3-C6 cycloalkynyls.

Herein, the “alkylene” includes divalent hydrocarbon groupscorresponding to the above “lower alkyl”.

Herein, the “alkenylene” includes divalent hydrocarbon groupscorresponding to the above “lower alkenyl”.

Herein, the “alkynylene” includes divalent hydrocarbon groupscorresponding to the above “lower alkynyl”.

Herein, the “C1-C5 alkylene which be intervened with a substituentselected from Substituent group a” includes (substituent selected fromSubstituent group a)-(C1-C5 alkylene), (C1-C5 alkylene)-(substituentselected from Substituent group a), (alkylene)-(substituent selectedfrom Substituent group a)-(alkylene) (provided that the sum of lengthsof both alkylene chains is an integer of 1 to 5).

Herein, the “aryl” which is used alone or in combination with otherterms includes monocyclic aromatic hydrocarbon groups or fused aromatichydrocarbon groups in which 2 or 3 aromatic rings are fused. Forexample, they are phenyl, 1-naphthyl, 2-naphthyl, anthryl and the like.

As the “aryl” in R¹, naphthyl is preferable, and 2-naphthyl isparticularly preferable.

As the “aryl” in R², phenyl is preferable.

As the “aryl” in R³, phenyl is preferable.

Herein, the “naphthyl” includes 1-naphthyl and 2-naphthyl.

Herein, the “aralkyl” which is used alone or in combination with otherterms is the abovementioned “lower alkyl” which is substituted with oneor more of the abovementioned “aryl”s, which may be incorporated at allpossible positions. For example, they are benzyl, phenylethyl (e.g.2-phenylethyl etc.), phenylpropyl (e.g. 3-phenylpropyl etc.),naphthylmethyl (e.g. 1-naphthylmethyl, 2-naphthylmethyl etc.),anthrylmethyl (e.g. 9-anthrylmethyl etc.), biphenylmethyl (e.g.4-biphenylmethyl etc.) and the like. Preferable examples are benzyl, andphenylethyl.

As the “aralkyl” in R², phenyl C1-C3 alkyls are preferable, and benzylis particularly preferable.

As the “aralkyl” in R³, phenyl C1-C6 alkyls and naphthyl C1-C6 alkylsare preferable. Further preferable are phenyl C1-C3 alkyls and naphthylC1-C3 alkyls, for example, benzyl, phenylethyl, 1-naphthylmethyl, and2-naphthylmethyl.

Herein, the “heteroaryl” which is used alone or in combination withother terms includes 5- to 6-membered aromatic rings containing, in thering, one or more atoms arbitrarily selected from oxygen atoms, sulfuratoms and nitrogen atoms, and these may be fused with cycloalkyl, aryl,non-aromatic heterocycle, or other heteroaryl, and may be fused at allpossible positions. For example, they are pyrrolyl (e.g. 1-pyrrolyl,2-pyrrolyl, 3-pyrrolyl), furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g.2-thienyl, 3-thienyl), imidazolyl (e.g. 2-imidazolyl, 4-imidazolyl,pyrazolyl (e.g. 1-pyrazolyl, 3-pyrazolyl), isothiazolyl (e.g.3-isothiazolyl), isoxazolyl (e.g. 3-isoxazolyl), oxazolyl (e.g.2-oxazolyl), thiazolyl (e.g. 2-thiazolyl), pyridyl (e.g. 2-pyridyl,3-pyridyl, 4-pyridyl), pyrazinyl (e.g. 2-pyrazinyl), pyrimidinyl (e.g.2-pyrimidinyl, 4-pyrimidinyl), pyridazinyl (e.g. 3-pyridazinyl),tetrazolyl (e.g. 1H-tetrazolyl), oxadiazolyl (e.g. 1,3,4-oxadiazolyl),thiadiazolyl (e.g. 1,3,4-thiadiazolyl), indolizinyl (e.g. 2-indolizinyl,6-indolizinyl), isoindolyl (e.g. 2-isoindolyl), indolyl (e.g. 1-indolyl,2-indolyl, 3-indolyl, 5-indolyl, 6-indolyl), indazolyl (e.g.3-indazolyl), purinyl (e.g. 8-purinyl), quinolizinyl (e.g.2-quinolizinyl), isoquinolyl (e.g. 3-isoquinolyl), quinolyl (e.g.2-quinolyl, 5-quinolyl), phthalazinyl (e.g. 1-phthalazinyl),naphthyridinyl (e.g. 2-naphthyridinyl), quinoxanyl (e.g. 2-quinoxanyl),quinazolinyl (e.g. 2-quinazolinyl), cinnolinyl (e.g. 3-cinnolinyl),pteridinyl (e.g. 2-pteridinyl), carbazolyl (e.g. 2-carbazolyl,3-carbazolyl), phenanthridinyl (e.g. 2-phenanthridinyl,3-phenanthridinyl), acridinyl (e.g. 1-acridinyl, 2-acridinyl),dibenzofuranyl (e.g. 1-dibenzofuranyl, 2-dibenzofuranyl,3-dibenzofuranyl), benzimidazolyl (e.g. 2-benzimidazolyl),benzisoxazolyl (e.g. 3-benzisoxazolyl), benzoxazolyl (e.g.2-benzoxazolyl), benzoxadiazolyl (e.g. 4-benzoxadiazolyl),benzisothiazolyl (e.g. 3-benzisothiazolyl), benzthiazolyl (e.g.2-benzthiazolyl, 5-benzthiazolyl), benzofuryl (e.g. 2-benzofuryl,3-benzofuryl, 5-benzofuryl), benzothienyl (e.g. 2-benzothienyl),thienopyrimidinyl, and the like.

As the “heteroaryl” in R¹, carbazolyl is preferable.

As the “heteroaryl” in R², pyridyl, thienyl, furyl, imidazolyl and thelike are preferable.

As the “heteroaryl” in R³, indolyl, imidazolyl, furyl, thienyl, and thelike are preferable.

Herein, the “heteroarylalkyl” is the abovementioned “lower alkyl”substituted with one or more of the abovementioned “heteroaryl”s at thearbitrary positions, and these can be incorporated at all possiblepositions. For example, they are oxazolylmethyl (e.g. 2-oxazolylmethyl,4-oxaszolylmethyl), thiazolylmethyl (e.g. 2-thiazolylmethyl,4-thiazolylmethyl), oxazolylethyl (e.g. 5-oxazolyl-2-ethyl),thiazolylyethyl (e.g. 5-thiazolyl-2-ethyl), benzoxazolylmethyl (e.g.benzoxazol-2-ylmethyl), benzothiazolylmethyl (e.g.benzothiazol-2-ylmethyl), indolylmethyl (e.g. indol-3-ylmethyl),imidazolylmethyl (e.g. 4-imidazolylmethyl), indazolylmethyl (e.g.1-indazolylmethyl), benzotriazolylmethyl (e.g. 1-benzotriazolylmethyl),benzoquinolylmethyl (e.g. 2-benzoquinolylmethyl), benzimidazolylmethyl(e.g. benzimidazol-2-methyl), pyridylmethyl (e.g. 4-pyridylmethyl),furylmethyl (e.g. furan-2-ylmethyl), thienylmethyl (e.g.thiophen-2-ylmethyl) and the like.

Examples of the “heteroarylalkyl” in R² are indolylmethyl (e.g.indol-3-ylmethyl), imidazolylmethyl (e.g. imidazol-5-ylmethyl),thienylmethyl (e.g. thiophen-2-ylmethyl), thiazolylmethyl (e.g.2-thiazolylmethyl, 4-thiazolylmethyl), pyridylmethyl and the like.

Examples of the “heteroarylalkyl” in R³ are indolylmethyl (e.g.indol-3-ylmethyl), imidazolylmethyl (e.g. imidazol-5-ylmethyl),benzoxazolylmethyl (e.g. benzoxazol-2-ylmethyl), benzothiazolylmethyl(e.g. benzothiazol-2-ylmethyl), benzimidazolylmethyl (e.g.benzimidazol-2-ylmethyl), thienylmethyl (e.g. thiophen-2-ylmethyl),thiazolylmethyl (e.g. 2-thiazolylmethyl, 4-thiazolylmethyl) and thelike.

Herein, a term “non-aromatic hydrocarbon group” which is used alone orin combination with other terms includes cycloalkyls, cycloalkenyls orcycloalkynyls, or cyclic groups in which they are fused with theabovementioned “aryl”. For example, they are cyclobutyl, cyclopentyl,cyclohexyl, indanyl, tetrahydronaphthyl and the like.

As the “non-aromatic carbocyclic group” in Z, cyclobutyl is preferable.

Examples of the “non-aromatic carbocycle” in which R³ and R⁴ are takentogether with an adjacent carbon to form a 5- to 6-membered non-aromaticcarbocycle, are cycloalkane, cycloalkene and cycloalkyne. Cyclopentane,cyclohexane, and the like are preferable.

Herein, a term “non-aromatic heterocyclic group” which is used alone orin combination with other terms includes a non-aromatic 5- to 7-memberedring containing, in the ring, one or more atoms, arbitrarily selectedfrom oxygen atoms, sulfur atoms and nitrogen atoms, and the ring groupsin which two or more of the above rings are fused, and the ring groupsin which the abovementioned “ring” is fused with the abovementioned“aryl”. For example, they are pyrrolidinyl (e.g. 1-pyrrolidinyl,2-pyrrolidinyl), pyrrolinyl (e.g. 3-pyrrolinyl), imidazolidinyl (e.g.2-imidazolidinyl), imidazolinyl (e.g. imidazolinyl), pyrazolidinyl (e.g.1-pyrazolidinyl, 2-pyrazolidinyl), pyrazolinyl (e.g. pyrazolinydl,piperidyl (e.g. piperidino, 2-piperidyl), piperazinyl (e.g.1-piperazinyl), indolinyl (e.g. 1-indolinyl), isoindolinyl (e.g.isoindolinyl), morpholinyl (e.g. morpholino, 3-morpholinyl),tetrahydroquinolyl, tetrahydrofuryl, tetrahydropyranyl,1,3-benzodioxolanyl, 1,4-benzodioxanyl, 1-benzoxolanyl, oxetanyl,azetidinyl, diazetidinyl, chromanyl, and the like.

As the “non-aromatic heterocyclic group” in Z, oxetanyl, azetidinyl, anddiazetidinyl are preferable.

As the “non-aromatic heterocycle” in which R³ and R⁴ are taken togetherwith an adjacent carbon to form a 5- to 6-membered non-aromaticheterocycle, tetrahydropyran and the like are preferable.

The “nitrogen-containing heterocycle optionally further containing anitrogen atom, an oxygen atom, and/or a sulfur atom in a ring” in the Bring means a nitrogen-containing heterocycle optionally furthercontaining a nitrogen atom, an oxygen atom, and/or a sulfur atom in thering, in addition to a nitrogen atom on the B ring. The“nitrogen-containing heterocycle” includes monocyclic 5- to 8-memberednitrogen-containing heterocycles, and bridged nitrogen-containingheterocycles. Preferable are nitrogen-containing heterocyclesrepresented by the formula:

(wherein, X is a carbon atom or a nitrogen atom, a C ring is a 5- to8-membered nitrogen-containing heterocycle or bridged ring, R⁷ ishalogen, lower alkyl, cycloalkyl, lower alkenyl, lower alkynyl, loweralkyloxy, lower alkenyloxy, lower alkylthio, halo lower alkyl, halolower alkyloxy, halo lower alkylthio, hydroxy, hydroxy lower alkyl,mercapto, carboxy, lower alkyloxycarbonyl, lower alkylsulfonyl, acyl,acyloxy, nitro, cyano, optionally substituted amino, or optionallysubstituted aminocarbonyl; m is an integer of 0 to 3). Furtherpreferable are nitrogen-containing heterocycles represented by theformula:

(wherein R⁷ and m are defined above). Particularly preferable arenitrogen-containing heterocycles represented the formula:

(wherein R⁷ and m are defined above).

Herein, “halogen” means fluorine, chlorine, bromine and iodine.Preferable are fluorine, chlorine, and bromine.

Herein, examples of the “lower alkyloxy” are methyloxy, ethyloxy,n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, s-butyloxy,t-butyloxy, n-pentyloxy, n-hexyloxy, and the like. Preferable is C1-C6alkyloxy. Further preferable is C1-C3 alkyloxy.

Herein, examples of the “lower alkenyloxy” are vinyloxy, allyloxy,propenyloxy, 3-butenyloxy, 2-butenyloxy (crotonyloxy, isocrotonyloxy),1-butenyloxy, isopentenyloxy and the like. C2-C3 alkenyloxy ispreferable.

Herein, examples of the “lower alkylthio” are methylthio, ethylthio,propylthio, isopropylthio, butylthio, s-butylthio, isobutylthio,t-butylthio and the like. C1-C3 alkylthio is preferable.

Herein, a term “halo lower alkyl” which is used alone or in combinationwith other terms includes the abovementioned “lower alkyl”, 1 to 8atoms, preferably 1 to 5 atoms of which are substituted with theabove-mentioned “halogen”. For example, they are trifluoromethyl,trichloromethyl, difluoroethyl, trifluoroethyl, dichloroethyl,trichloroethyl and the like. Preferable examples are C1-C3 lower alkyls,1 to 5 atoms of which are substituted with the “halogen”. Particularlypreferable examples are trifluoromethyl.

Herein, as the “halo lower alkyloxy”, C1-C3 lower alkyloxys, 1 to 5atoms of which are substituted with the “halogen”, is preferable.Particularly preferable examples are trifluoromethyloxy.

Herein, as the “halo lower alkylthio”, C1-C3 lower alkylthios, 1 to 5atoms of which are substituted with the “halogen”, is preferable.Particularly preferable examples are trifluoromethylthio.

Herein, a term “hydroxy lower alkyl” includes the above-mentioned “loweralkyl” substituted with a hydroxy group. For example, they arehydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl,2-hydroxypropyl, 3-hydroxypropyl and the like. Preferable examples arehydroxymethyl, 1-hydroxyethyl, and 2-hydroxyethyl.

Herein, examples of the “lower alkyloxycarbonyl” are methyloxycarbonyl,ethyloxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl and thelike.

Herein, examples of the “lower alkylsulfonyl” are methylsulfonyl,ethylsulfonyl and the like. Preferable example is methylsulfonyl.

Herein, examples of the “aralkyloxy” are phenyl C1-C3 alkyloxy, naphthylC1-C3 oxy and the like. Preferable example is benzyl.

Herein, a term “lower alkyloxy lower alkyl” includes the abovementioned“lower alkyl” substituted with the abovementioned “lower alkyloxy”. Forexample, they are methyloxymethyl, ethyloxymethyl, propyloxymethyl,1-methyloxyethyl, 2-methyloxyethyl, 1-methyloxypropyl,2-methyloxypropyl, 3-methyloxypropyl, and the like. Preferable exampleis methyloxymethyl.

Herein, examples of the “aryloxy lower alkyl” are phenyloxymethyl,1-phenyloxyethyl, 2-phenyloxyethyl, 1-naphthyloxymethyl,2-naphtyloxymethyl and the like.

Herein, a term “acyl” which is used alone or in combination with otherterms includes alkylcarbonyl in which an alkyl moiety is theabovementioned “lower alkyl”, arylcarbonyl in which an aryl moiety isthe abovementioned “aryl”, and heteroarylcarbonyl in which a heteroarylmoiety is the abovementioned “heteroaryl”. For example, they are acetyl,propionyl, benzoyl, pyridylcarbonyl and the like. The “lower alkyl” andthe “aryl” may be substituted with a substituent described later.

Herein, examples of the “acyloxy” are acetyloxy, propionyloxy,benzoyloxy, and the like.

Herein, the “optionally substituted amino” which is used alone or incombination with other terms includes amino and amino, 1 or 2 atoms ofwhich are substituted with the abovementioned “lower alkyl”, theabovementioned “alalkyl”, the abovementioned “heteroarylalkyl”, theabove mentioned “lower alkylsulfonyl”, or the above mentioned “acyl”.Preferable examples are unsubstituted amino, and amino substituted with1 or 2 substituents selected from the group consisting of C1-C6 alkyl,phenyl C1-C3 alkyl, pyridyl C1-C3 alkyl, C1-C6 alkylsulfonyl, C1-C6alkylcarbonyl and arylcarbonyl. For example, they are amino,methylamino, dimethylamino, ethylmethylamino, diethylamino, benzylamino,methylsulfonylamino, acetylamino, benzoylamino and the like. Preferableexamples are amino, methylamino, dimethylamino, ethylmethylamino,diethylamino, methylsulfonylamino and acetylamino.

Herein, as the “optionally substituted aminocarbonyl”, unsubstitutedaminocarbonyl, or aminocarbonyl, 1 or 2 atoms of which are substitutedwith C1-C6 alkyl, is preferable. For example, they are aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, ethylmethylaminocarbonyl,diethylaminocarbonyl and the like. Preferable examples are aminocarbonyland dimethylaminocarbonyl.

Herein, examples of a substituent in the “optionally substituted loweralkyl” are lower alkylthio, cycloalkyl, carboxy, lower alkyloxy,hydroxy, mercapto, halogen, nitro, cyano, lower alkyloxycarbonyl, halolower alkyl, halo lower alkyloxy, optionally substituted amino,optionally substituted aminocarbonyl, acyl, acyloxy, a non-aromaticheterocyclic group optionally substituted with a substituent selectedfrom Substituent group b, aryloxy, aralkyloxy, lower alkylsulfonyl,guanidino, azo group, ureido optionally substituted with a substituentselected from Substituent group b, carbamoyl and the like. These maysubstitute at one or more of all possible positions.

Substituent group b: lower alkyl, cycloalkyl, lower alkenyl, loweralkynyl, hydroxy, lower alkyloxy, mercapto, lower alkylthio, loweralkenyloxy, halogen, nitro, cyano, carboxy, lower alkyloxycarbonyl, halolower alkyl, halo lower alkyloxy, halo lower alkylthio, optionallysubstituted amino, optionally substituted aminocarbonyl, acyl, acyloxy,aryl, heteroaryl, non-aromatic heterocycle, aralkyl, loweralkylsulfonyl, guanidino, azo group, and ureido.

As a substituent of the “optionally substituted lower alkyl” in R²,hydroxy, lower alkyloxy, and a non-aromatic heterocyclic groupoptionally substituted with a substituent selected from Substituentgroup b are preferable.

As a substituent of the “optionally substituted lower alkyl” in R³,lower alkyloxy, lower alkylthio, cycloalkyl, carboxy, halogen, hydroxy,carbamoyl, and mercapto are preferable.

Herein, examples of the substituents in the “optionally substitutedaryl”, the “optionally substituted heteroaryl”, the “optionallysubstituted aralkyl”, and the “optionally substituted heteroarylalkyl”in R² and R³ are lower alkyl optionally substituted with a substituentselected from Substituent group b, cycloalkyl, lower alkenyl, loweralkynyl, hydroxy, lower alkyloxy, mercapto, lower alkylthio, loweralkenyloxy, halogen, nitro, cyano, carboxy, lower alkyloxycarbonyl, halolower alkyl, halo lower alkyloxy, halo lower alkylthio, optionallysubstituted amino, optionally substituted aminocarbonyl, acyl, acyloxy,aryl optionally substituted with a substituent selected from Substituentgroup b, hetroaryl optionally substituted with a substituent selectedfrom Substituent group b, non-aromatic heterocycle optionallysubstituted with a substituent selected from Substituent group b,aralkyl optionally substituted with a substituent selected fromSubstituent group b, lower alkylsulfonyl, guanidino, azo group, andureido optionally substituted with a substituent selected fromSubstituent group b. These can substitute at one or more of all possiblepositions.

Substituent b: lower alkyl, cycloalkyl, lower alkenyl, lower alkynyl,hydroxy, lower alkyloxy, mercapto, lower alkylthio, lower alkenyloxy,halogen, nitro, cyano, carboxy, lower alkyloxycarbonyl, halo loweralkyl, halo lower alkyloxy, halo lower alkylthio, optionally substitutedamino, optionally substituted aminocarbonyl, acyl, acyloxy, aryl,heteroaryl, non-aromatic heterocycle, aralkyl, lower alkylsulfonyl,guanidino, azo group, and ureido

As a substituent of the “optionally substituted aryl” in R², hydroxy,lower alkyloxy, halogen, and halo lower alkyl are preferable.

As a substitutent of the “optionally substituted aryl” in R³, hydroxy ispreferable.

As a substituent of the “optionally substituted heteroaryl” in R²,hydroxy, lower alkyloxy, halogen, and halo lower alkyl and preferable.

As a substitutent of the “optionally substituted heteroaryl” in R³,hydroxy and halogen are preferable.

As a substituent of the “optionally substituted aralkyl” in R², hydroxy,lower alkyloxy, halogen, halo lower alkyl, and nitro are preferable.

As a substituent of the “optionally substituted aralkyl” in R³, hydroxy,halogen, nitro, lower alkyloxy, halo lower alkyl, and carboxy loweralkyloxy are preferable.

As a substituent of “optionally substituted heteroarylalkyl” in R²,hydroxy, lower alkyloxy, halogen, and halo lower alkyl are preferable.

As a substituent of the “optionally substituted heteroarylalkyl” in R³,halogen, hydroxy, and carboxy are preferable.

Herein, examples of the substituents in the “optionally substitutedaryl”, the “optionally substituted heteroaryl”, the “optionallysubstituted non-aromatic carbocyclic group”, the “optionally substitutednon-aromatic heterocyclic group”, the “optionally substituted naphtyl”,the “optionally substituted carbazolyl” in R¹ are halogen, lower alkyloptionally substituted with a substituent selected from substituentgroup e, lower alkyloxy optionally substituted with a substituentselected from Substituent group f, cycloalkyl, lower alkenyl optionallysubstituent with carboxy, lower alkynyl, lower alkenyloxy, loweralkylthio, halo lower alkyl, halo lower alkyloxy, halo lower alkylthio,hydroxy, hydroxy lower alkyl, mercapto, carboxy, lower alkyloxycarbonyl,lower alkylsulfonyl, acyl, acyloxy, nitro, cyano, oxo, hydroxyimino,lower alkyloxyimino, optionally substituted amino, optionallysubstituted aminocarbonyl, aryl optionally substituted with asubstituent selected from Substituent group b, heteroaryl optionallysubstituted with a substituent selected from Substituent group b,aryloxy optionally substituted with a substituent selected fromSubstituent group b, aralkyloxy optionally substituted with asubstituent selected from Substituent group b, lower alkyloxy loweralkyl, aryloxy lower alkyl optionally substituted with a substituentselected from Substituent group b, ureido optionally substituted with asubstituent selected from Substituent group b, and non-aromaticheterocyclic group optionally substituted with a substituent selectedfrom Substituent group b. These can substitute at one or more of allpossible positions.

Substituent group b: lower alkyl, cycloalkyl, lower alkenyl, loweralkynyl, hydroxy, lower alkyloxy, mercapto, lower alkylthio, loweralkenyloxy, halogen, nitro, cyano, carboxy, lower alkyloxycarbonyl, halolower alkyl, halo lower alkyloxy, halo lower alkylthio, optionallysubstituted amino, optionally substituted aminocarbonyl, acyl, acyloxy,aryl, heteroaryl, non-aromatic heterocycle, aralkyl, loweralkylsulfonyl, guanidino, azo group, and ureido

Substituent group e carboxy, cyano, lower alkyloxyimino, and optionallysubstituted aminocarbonyl

Substituent group f: hydroxy, lower alkyloxy, cycloalkyl, aryl, carboxy,and optionally substituted aminocarbonyl

Herein, as the “optionally substituted naphtyl” in R¹, 2-naphtyl whichhas no substituents either at the position 5 or 8, is preferable.

Herein, as the “optionally substituted carbazolyl” in R¹, unsubstitutedcarbozolyl is preferable.

As the present compound, particularly, compounds represented by thefollowing A) to AC) are preferable.

A) A compound represented by the general formula (IV):

[wherein R¹¹ is optionally substituted naphthyl or optionallysubstituted carbazolyl;Z¹ is —C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)═C(R⁹)—, —C═C—, —O—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—O—, —S—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—S—, —SO—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—SO—, —SO₂—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—, —N(R¹⁰)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—N(R¹⁰)—, —N(R¹⁰)—C(═O)—, —C(═O)—N(R¹⁰)—, —N(R¹⁰)—SO₂—,—SO₂—N(R¹¹)—, —C(R⁸)(R⁹)—C(═O)—, —C(═O)—C(R⁸)(R⁹)—, or —C(═O)C(═O)—(wherein, R⁸, R⁹, and R¹⁰ are each independently a hydrogen atom, orlower alkyl);R¹² is a hydrogen atom or lower alkyl;R¹³ is a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl,s-butyl, isobutyl, t-butyl, hydroxymethyl, 1-hydroxyethyl,2-hydroxyethyl, carboxymethyl, carboxyethyl, methyloxymethyl,methylthiomethyl, 2-methylthioethyl, phenyl, 4-hydroxyphenyl,4-fluorophenyl, 4-methyloxyphenyl, benzyl, 4-hydroxybenzyl,4-fluorobenzyl, 4-chlorobenzyl, 4-methoxybenzyl, indol-3-ylmethyl,1-carboxymethylindol-3-ylmethyl, thiazol-4-ylmethyl,carboxymethyloxybenzyl, or cyclopropylmethyl,R¹⁴ is a hydrogen atom; orR¹³ and R¹⁴ may be taken together with an adjacent carbon to form thering represented by the formula:

R¹⁵ is hydroxy or lower alkyloxy;R¹⁶ and R¹⁷ are each independently halogen, lower alkyl, lower,alkyloxy, or hydroxy;x and y are each independently an integer of 0 to 3],an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.B) A compound represented by the general formula (V):

wherein, R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x, and y are as definedin A), an optically active isomer, a pharmaceutically acceptable salt ora solvate thereof.C) A compound represented by the general formula (VI):

wherein R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x, and y are as definedin A), an optically active isomer, a pharmaceutically acceptable salt,or a solvate thereof.D) A compound represented by the general formula (VII):

wherein R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x, and y are as definedin A), an optically active body isomer, a pharmaceutically acceptablesalt, or a solvate thereof.E) A compound represented by the general formula (VIII):

wherein R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x, and y are as definedin A), an optically active body isomer, a pharmaceutically acceptablesalt, or a solvate thereof.F) A compound represented by the general formula (IX):

wherein R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x, and y are as definedin A) an optically active isomer, a pharmaceutically acceptable salt, ora solvate thereof.G) A compound represented by the general formula (X):

wherein R¹¹, Z¹, R¹², R¹³. R¹⁴, R¹⁵, R¹⁶, R¹⁷, x, and y are as definedin A)] an optically active isomer, a pharmaceutically acceptable salt,or a solvate thereof.H) A compound represented by the general formula (XI)

wherein R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x and y are as defined inA), an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.1) A compound represented by the general formula (XII):

wherein R¹¹, Z¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x and y are as defined inA) an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.J) A compound represented by the general formula (XIII)

wherein R¹¹, Z¹, R¹²R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, x and y are as defined inA), an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.K) The compound described in any of A) to J), wherein R¹¹ is optionallysubstituted naphthyl, an optically active isomer, a pharmaceuticallyacceptable salt or a solvate thereof.L) The compound described in any of A) to K), wherein R¹¹ is a grouprepresented by the formula:

wherein, R²⁶ is a hydrogen atom, optionally substituted lower alkyl,optionally substituted lower alkenyl, hydroxy, optionally substitutedlower alkyloxy, carboxy, acyl, optionally substituted amino, optionallysubstituted aminocarbonyl or non-aromatic heterocycle;R²⁷ is halogen, cyano, or acyl;n² is an integer of 0 to 2, and R²⁷ can substitute at all incorporablering-constituting atoms, an optically active isomer, a pharmaceuticallyacceptable salt, or a solvate thereof. Among the above compounds, thecompounds in which n² is 0 are preferable.M) The compound described in any of A) to L), wherein R¹¹ is a grouprepresented by the formula:

wherein R²⁸ is a hydrogen atom; lower alkyl optionally substituted withcarboxy or lower alkyloxyimino; lower alkenyl optionally substitutedwith carboxy; hydroxy; lower alkyloxy optionally substituted withcycloalkyl, hydroxy, lower alkyloxy, carboxy, or aminocarbonyloptionally substituted with 1 or 2 lower alkyl(s); carboxy; acyl; aminooptionally substituted with 1 or 2 acyl(s) or lower alkylsulfonyl;aminocarbonyl optionally substituted with 1 or 2 lower alkyl(s); ornon-aromatic heterocycle;R²⁹ is halogen, cyano, or acyl;n³ is an integer of 0 to 2, and R²⁹ can substitute at all incorporablering-constituting atoms, an optically active isomer, a pharmaceuticallyacceptable salt, or a solvate thereof. Among the above compounds, thecompounds in which n³ is 0 are preferable.N) The compound described in any of A) to K), wherein R¹¹ is a grouprepresented by the formula:

wherein R²⁶, R²⁷, and n² are as defined in L),an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof. Among the above compounds, the compound in which n² is0 are preferable.O) The compound described in any of A) to K), and N), wherein R¹¹ is agroup represented by the formula:

wherein R²⁸, R²⁹, and n³ are as defined in M), an optically activeisomer, a pharmaceutically acceptable salt, or a solvate thereof. Amongthe above compounds, the compounds in which n³ is 0 are preferable.P) The compound described in any of A) to K), wherein R¹¹ is a grouprepresented by the formula:

wherein R²⁶, R²⁷, and n² are as defined in L),an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof. Among the above compounds, the compounds in which n² is0 are preferable.Q) The compound described in any of A) to K), and P), wherein R¹¹ is agroup represented by the formula:

wherein R²⁸, R²⁹ and n³ are as defined in M), an optically activeisomer, a pharmaceutically acceptable salt, or a solvate thereof. Amongthe above compounds, the compounds in which n³ is 0 are preferable.R) The compound described in any of A) to K), wherein R¹¹ is optionallysubstituted carbazolyl, an optically active isomer, a pharmaceuticallyacceptable salt, or a solvate thereof. Among the compounds, thecompounds in which R¹¹ is unsubstituted carbazolyl are preferable.S) The compound described in any of A) to R), wherein Z¹ is —CH₂—CH₂—,—CH═CH—, —C≡C—, —O—CH₂—, —CH₂—O—, —S—CH₂—, —CH₂—S—, —SO—CH₂—, —CH₂—SO—,SO₂—CH₂—, —CH₂—SO₂—, —N(R¹⁰)—CH₂—, —CH₂—N(R¹⁰)—, —NH—C(═O)—, —C(═O)—NH—,—CH₂—C(═O)—, —C(═O)—CH₂—, or —C(═O)C(═O)—, an optically active isomer, apharmaceutically acceptable salt, or a solvate thereof.T) The compound described in any of A) to S), wherein Z¹ is —CH₂—CH₂—,—CH═CH—, —C≡C—, —O—CH₂—, or —CH₂—O—, an optically active isomer, apharmaceutically acceptable salt, or a solvate thereof.U) The compound described in any of A) to T), wherein Z¹ is —CH₂—CH₂—,—CH═CH— or —C≡C—, an optically active isomer, a pharmaceuticallyacceptable salt, or a solvate thereof.V) The compound described in any of A) to U), wherein Z¹ is —C≡C—, anoptically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.W) The compound described in any of A) to V), wherein R¹² is a hydrogenatom, an optically active isomer, a pharmaceutically acceptable salt, ora solvate thereof.X) The compound described in any of A) to W), wherein R¹³ is a hydrogenatom, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl,t-butyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, carboxymethyl,carboxyethyl, methyloxymethyl, methylthiomethyl, 2-methylthioethyl,phenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4-methyloxyphenyl, benzyl,4-hydroxybenzyl, 4-fluorobenzyl, 4-chlorobenzyl, 4-methoxybenzyl,indol-3-ylmethyl, 1-carboxymethylindol-3-ylmethyl, thiazol-4-ylmethyl,carboxymethyloxybenzyl, or cyclopropylmethyl, and R¹⁴ is a hydrogenatom, an optically active isomer, a pharmaceutically acceptable salt, ora solvate thereof.

Y) The compound described in any of A) to X), wherein R¹³ is methyl,ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl,hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, carboxymethyl,carboxyethyl, methyloxymethyl, methylthiomethyl, 2-methylthioethyl,phenyl, 4-hydroxyphenyl, 4-fluorophenyl, 4-methyloxyphenyl, benzyl,4-hydroxybenzyl, 4-fluorobenzyl, 4-chlorobenzyl, 4-methoxybenzyl,indol-3-ylmethyl, 1-carboxymethylindol-3-ylmethyl, thiazol-4-ylmethyl,carboxymethyloxybenzyl, or cyclopropylmethyl, and R¹⁴ is a hydrogenatom, an optically active isomer, a pharmaceutically acceptable salt, ora solvate thereof.

Z) The compound described in any of A) to W), wherein R¹³ and R¹⁴ aretaken together with an adjacent carbon to form a ring represented by theformula:

an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.AA) The compound described in any of A) to Z), wherein R¹⁵ is hydroxy,an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.AB) The compound described in any of A), F), and K) to AA), wherein thegroup represented by the formula:

is the group represented by the formula:

wherein in R¹⁸, R¹⁹, R²⁰, and R²¹, i) all are hydrogen atoms, or ii)only R¹⁸ is lower alkyl, and all of the rest are hydrogen atoms, iii)only R¹⁹ is lower alkyl, and all of the rest are hydrogen atoms, or iv)R¹⁸ and R²⁰ are each independently lower alkyls, and all of the rest arehydrogen atoms, or v) R¹⁸ and R²¹ are each independently lower alkyls,and all of the rest are hydrogen atoms, or yl) R¹⁹ and R²¹ are eachindependently lower alkyls, and all of the rest are hydrogen atoms, anoptically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.AC) The compound described in any of B), G), and K) to AA), wherein thegroup represented by the formula:

is the group represented by the formula:

wherein R²² is a hydrogen atom, halogen, hydroxy, or lower alkyloxy, anoptically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.

EFFECT OF THE INVENTION

It was found that certain novel sulfonamide derivatives exhibit theMMP-13 selective inhibiting activity. These derivatives can be utilizedas an agent for treating or preventing a disease resulting from, orassociated with MMP-13, particularly, osteoarthritis (OA). Also, theinvented compounds have excellent profile as a medicament, such asrelatively low protein binding rate, excellent solubility, good oralabsorbability, and/or low toxicity.

BEST MODE FOR CARRYING OUT THE INVENTION

The present compound can be synthesized according to the methoddescribed in WO97/27174, WO00/46189 and the like, and the known method.As the methods for synthesizing the invented compounds, Method A andMethod B are exemplified below.

(wherein R¹, R², R³, R⁴, R⁶, R⁷, m and n are as defined above; R²³ is aprotecting group of a carboxyl group; and Hal¹ is halogen)

(Step 1)

Some compounds of the starting material represented by the formula (i)are commercially available. The other compounds can be synthesizedaccording to the method described in Tetrahedron Lett. 39 (1998)617-620.

Some compounds of the starting material represented by the formula (ii)are commercially available.

A compound represented by the formula (III) can be obtained by reactinga compound represented by the formula (i) or a salt thereof, and acompound represented by the formula (ii) at ice-bath temperature to 80degree, preferably 0 degree to 30 degree, for 1 to 38 hours, preferably3 to 24 hours in a solvent such as acetonitrile, tetrahydrofuran,N,N-dimethylformamide and the like, in the presence of a base such astriethylamine, diisopropylethylamine, potassium carbonate and the like.

(Step 2)

compound represented by the formula (iv) can be obtained by reacting thecompound represented by the formula (iii) with methyltrifluoromethanesulfonate at ice-bath temperature to room temperaturefor 1 to 24 hours, preferably 1 to 5 hours.

(Step 3)

Some of the starting amino acids and their acid addition salts (e.g.hydrochloride, p-toluenesulfonate, trifluoroacetate) represented by theformula (v) are commercially available. The other amino acids and theiracid addition salts can be synthesized according to the method for aminoacid synthesis, described in Experimental Chemistry Course, vol. 22, 4edition (edited by The Chemical Society of Japan), or the methoddescribed in J. Med. Chem. 38, 1689-1700 (1995) Gary M. Ksander et. al.and the like.

In addition, some of sulfonylating reagents (e.g. sulfonic acid halide)are commercially available and the other reagent can be synthesizedaccording to the method described in New Experimental Chemistry Coursevol. 14, p 1787, (1978), Synthesis 852-854 (1986) Tatsuo Hamada et. al.and the like.

The protecting groups for carboxyl groups include, for example, anesterified carboxyl group (e.g. methyl ester, tert-butyl ester, benzylester). Removal of these protecting groups can be performed byhydrolysis in the presence of an acid (e.g. hydrochloric acid,trifluoroacetic acid) or a base (e.g. sodium hydroxide etc), orhydrogenolysis (e.g. in the presence of 10% palladium-carbon catalyst),depending on the protecting groups.

Solvents for the sulfonylation include dimethylformamide,tetrahydrofuran, dioxane, dimethyl sulfoxide, acetonitrile, water and amixed solvent thereof, and a mixed solvent of a water-insoluble solvent(e.g. benzene, dichloromethane) and the aforementioned solvent.

The base used for the sulfonylation is an organic base such astriethylamine, N-methylmorpholine and the like, or an inorganic basesuch as sodium hydroxide, potassium hydroxide, potassium carbonate andthe like. The reaction temperature is usually ice-bath temperature roomtemperature. When R³ and R⁴ are groups having a substituent which isharmful for sulfonylation (e.g. hydroxy, mercapto, amino, guanidino),the group can be protected in advance by the method described inProtective Groups in Organic Synthesis, Theodora W Green (John Wiley &Sons), and the protecting group may be removed at a desirable stage.

(Step 4)

By reacting with an optionally substituted naphthyl derivative having anethynyl group such as ethynylnaphthalene and the like in the presence ofa palladium catalyst (e.g. Pd(Ph₃P)₂Cl₂ etc.), a divalent copper reagent(e.g. CuI etc.), and an organic base (e.g. triethylamine,diisopropylethylamine etc.) in a solvent such as dimethylformamide,toluene, xylene, benzene, tetrahydrofuran and the like (Sonogashirareaction), the compound (vi) can be converted into the desired compound.

The reaction temperature is room temperature to 100° C., preferably roomtemperature to 80° C., and the reaction time is 3 to 30 hours,preferably 10 to 20 hours. When the optionally substituted naphthylderivative has a substituent which is harmful to the present reaction,the group can be protected in advance by the method described inProtective Groups in Organic Synthesis, Theodora W Green (John Wiley &Sons), and the protecting group may be removed at a preferable stage.

(Step 5)

The desired N—R² analogs can be obtained by adding alkyl halide (e.g.methyl iodide, ethyl iodide etc.) or aralkyl halide (e.g. benzylchloride, benzyl bromide etc.) to the compound (vii) at ice-bathtemperature to 80° C., preferably at ice-bath temperature to roomtemperature, in a solvent such as dimethylformamide, tetrahydrofuran,dioxane and the like, and by stirring the mixture for 3 to 30 hours,preferably 10 to 20 hours.

(Step 6)

The compound represented by the general formula (I) can be synthesizedby deprotecting the protective group of the compound (viii) according toa conventional method.

(wherein R¹, R³, R⁴, R⁶, R⁷, R²³, m and n are as defined above; R¹⁰ is aprotecting group for a carboxyl group; Hal¹ and Hal² are eachindependently halogen; Pro is a protecting group such as Boc etc.)

(Step 1)

Some compounds of the starting material represented by the formula (x)are commercially available.

Some compounds of the starting material represented by the formula (xi)are commercially available. The other compounds can be synthesizedaccording to the method described in Tetrahedron Lett. 37 (1996)6965-6968.

A compound represented by the formula (xii) can be obtained by reactingthe compound represented by the formula (x) or a salt thereof and acompound represented by the formula (xi) at ice-bath temperature to 110degree, preferably 0 degree to 80 degree for 1 to 36 hours, preferably 1to 24 hours in the presence of a base such as potassium carbonate,cesium carbonate, sodium hydroxide and the like, in a solvent such asdimethylformamide, 1,4-dioxane, dichloromethane and the like.

(Step 2)

Some compounds of the starting material represented by the formula(xiii) are commercially available. The other compounds can besynthesized according to the method described in Angew Chem, Int Ed 37(1998) 325-329.

A compound represented by the formula (xiv) can be obtained by reactinga compound represented by the formula (xii) and a compound representedby the formula (xiii) at room temperature to 150 degree, preferably roomtemperature to 120 degree, for 1 to 24 hours, preferably 1 to 8 hours,in the presence of a base such as sodium t-butoxide, cesium carbonateand the like, a palladium catalyst such as palladium acetate and thelike, and a ligand such as tri-t-butylphosphine, triphenylphosphine andthe like in a mixed solvent of toluene, and N-methylpiperidone,N,N-dimethylformamide, 1,4-dioxane and the like.

(Step 3)

Step 3 is a step of deprotecting a protecting group. The step can beperformed by a method which is usually conducted.

(Step 4)

Step 4 can be conducted by the same method as the Method A Step 1.

(Step 5)

Step 5 can be conducted by the same method as the Method A Step 2.

(Step 6)

Step 6 can be conducted by the same method as the Method A Step 3.

(Step 7)

Step 7 can be conducted by the same method as the Method A Step 6.

The compound represented by the general formula (iii) can be alsosynthesized according to the aforementioned method, the method describedin WO 97/27174, WO 00/46189 and the like, and the known method.

The therapeutic effect of the present compound regarding osteoarthritisand adjuvant arthritis can be confirmed by the following method.

A) Osteoarthritis

Using a 12 week-old female Hartley guinea pig (Charles RiverLaboratories Japan, Inc.), a right knee joint meniscus and an insidecollateral ligament are excised according to the method of Meacock etal. (J. Exp. Path. 71: 279-293, 1990), by which a guinea pig kneeosteoarthritis model is prepared. From the following date of operation,a 0.5% methylcellulose solution as a solvent, or a 30 mg/kg testcompound solution is orally administered once a day every day for 10days.

On the following day of the final administration date, a right osfemoris distal portion and a cnemis proximal part are taken. After ajoint cartilage surface is stained with India ink (manufactured byKuretake Co, Ltd.), a cartilage surface is photographed with a digitalcamera (manufactured by Nikon Corporation). Assessment of compounds isperformed by scoring a degree of an OA lesion on a joint cartilagesurface using a photographed image by a blind method.

In addition, similarly, the effect can be also confirmed by oraladministration every day for 6 weeks using a 12 week-old female NZWrabbit (KITAYAMA LABES Co., Ltd.) or a 12 week-old female SD rat (CLEAJapan, Inc.).

B) Adjuvant Arthritis

Using a 7-week old female Lewis rat (manufactured by Charles RiverLaboratories Japan, Inc.), and according to the method of Fletcher etal. (J. Pharmacol. Exp. Ther. 284(2): 714-721), dead mycobacteriumbutyricum is administered to a right posterior limb footpad to prepare arat adjuvant arthritis model. From the following day of administration,a 0.5% methylcellulose solution which is a solvent, or a 30 mg/kg testcompound solution is orally administered once a day. After 21 days fromadministration, a degree of posterior limb bloating is measured using avolume recording meter (manufactured by Shionogi & Co., Ltd.), a spleenand a thymus are taken, and their weight are measured. In addition, bothposterior limbs are subjected to X-ray photographing (manufactured byOHMIC Co., Ltd.). Determination of X-ray image is performed by a blindmethod using a score from 0 (normal) to 3 (bone/cartilage completedestruction), depending on a degree of joint destruction.

Herein, the “solvate” includes, for example, a solvate with an organicsolvent, a hydrate and the like. When a hydrate is formed, an arbitrarynumber of water molecules may be coordinated.

The “present compound” also includes a pharmaceutically acceptable salt,and a solvate thereof. For example they are salts with alkali metals(lithium, sodium, potassium etc.), alkaline earth metals (magnesium,calcium etc.), ammonium, organic bases and amino acids, and salts withinorganic acids (hydrochloric acid, hydrobromic acid, phosphoric acid,sulfuric acid etc.), and organic acids (acetic acid, citric acid, maleicacid, fumaric acid, benzenesulfonic acid, p-toluenesulfonic acid etc.).These salts can be formed by the method which is conventionallyperformed.

And, the present compound is not limited to a specified isomer, andincludes all possible isomers (e.g. optically active body) or racemates.

The present compound does not exhibit the inhibiting activity on MMP-2and MMP-9, but exhibits the selective and excellent MMP-13 inhibitingactivity as described in Test Example described later.

The present compound can be used as a remedy for osteoarthritis,arthritis rheumatism, adjuvant arthritis, periodontitis, cirrhosis,osteoporosis, bone resorption, gingivitis, large intestine-rectumcancer, squamous epithelial cancer, epithelial cell cancer, prostatecancer, ovary cancer, tongue cancer, endometrium cancer, or stomachcancer.

When the present compound is administered to a human for the purpose oftreating the aforementioned diseases, it can be orally administered aspowders, granules, tablets, capsules, pills, solutions or the like, orcan be parenterally administered as injectables, suppositories,transdermally absorbing agents, inhalants or the like. And,pharmaceutical additives suitable for a dosage form, such as excipients,binders, wetting agents, disintegrating agents, lubricants and the like,can be, if necessary, mixed into an effective amount of the presentcompound to obtain pharmaceutical preparations. In the case ofinjectables, they are sterilization-treated together with suitablecarriers to obtain preparations.

A dose is different depending on condition of a patient, anadministration route, an age and a weight of a patient and, when orallyadministered to an adult, the dose is usually 0.1 to 100 mg/kg/day,preferably 1 to 20 mg/kg/day.

The present invention will be explained in more detail below by way ofExamples and Test Examples, but the present invention is not limited tothem.

EXAMPLES

In Examples, following abbreviations are used.

Me: methylTf: trifluoromethanesulfonyl

Boc: t-butoxycarbonyl

Examples 1 Synthesis of(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-pentanoicacid (I-1)

Step 1

To a solution of 1-(4-bromophenyl)piperazine hydrochloride (1) (5 g,18.0 mmol) and triethylamine (2.8 mL, 20.1 mmol) in acetonitrile (80 mL)was added 3-(imidazol-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate(2; J. Org. Chem., 68, 115 (2003)) (9.8 g, 27.0 mmol), and the mixturewas stirred at room temperature for 24 hours. The reaction mixture waspoured into ice-water, this was extracted with ethyl acetate, and theorganic layer was washed with water. After dried over anhydrous sodiumsulfate, the organic layer was concentrated under reduced pressure. Theresidue was subjected to silica gel chromatography, and the fractionseluted with hexane/ethyl acetate=1/1 were collected to give a pale browncompound (3) (2.91 g, yield 45.3%). The compound (3) was used in a nextstep without purification.

mp 153-154° C.

¹H NMR (CDCl₃) δ: 3.20-3.26 (m, 4H), 3.36-3.40 (m, 4H), 6.76 (d, J=9.0Hz, 2H), 7.22 (m, 1H), 7.29 (m, 1H), 7.37 (d, J=9.0 Hz, 2H), 8.07 (m,1H).

Step 2

To a solution of the compound (3) (4.82 g, 13.0 mmol) in dichloromethane(80 mL) was added methyl trifluoromethanesulfonate (1.6 mL, 14.1 mmol)under ice cooling, and this was stirred for 2.5 hours. The precipitatedsolid was collected by filtration, washed with dichloromethane and,then, n-hexane, and air-dried to give a compound (4) (6.3 g, yield90.6%). The compound (4) was used in a next step without purification.mp 154-156° C.

¹H-NMR (DMSO-d₆) δ: 3.28-3.35 (m, 4H), 3.46-3.53 (m, 4H), 3.88 (s, 3H),6.93 (d, J=9.0 Hz, 2H), 7.38 (d, J=9.0 Hz, 2H), 7.98 (m, 1H), 8.24 (m,1H), 9.85 (s, 1H).

Step 3

To a solution of the compound (4) (0.8 g, 1.49 mmol) in acetonitrile (8mL) were added L-norvaline methyl ester hydrochloride (5) (0.38 g, 2.27mmol) and, then, triethylamine (0.31 mL, 2.22 mmol) at room temperature,and the mixture was stirred for 40 hours. The reaction mixture waspoured into ice water, and extracted with ethyl acetate. The organiclayer was washed with water, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel chromatography, and the fractions eluted with ethylacetate/hexane=1/3 were collected to give a pale yellow compound (6)(0.35 g, yield 53.8%).

The compound (6) was used in a next step without purification.

¹H NMR (CDCl₃) δ: 0.95 (t, J=7.2 Hz, 3H), 1.35-1.50 (m, 2H), 1.60-1.85(m, 2H), 3.13-3.22 (m, 4H), 3.32-3.40 (m, 4H), 3.77 (s, 3H), 3.98 (m,1H), 4.91 (d, J=9.6 Hz, 1H), 6.82 (d, J=9.0 Hz, 2H), 7.37 (d, J=9.0 Hz,2H).

Step 4

To a solution of the compound (6) (0.34 g, 0.78 mmol) indimethylformamide (5 mL) was added 2-ethynyl-6-methoxynaphthalene (7)(0.19 g, 1.04 mmol), and this was degassed under the nitrogen gasatmosphere. Then, bis(triphenylphosphine)palladium (II) chloride (0.06g, 0.08 mmol), copper (I) iodide (0.03 g, 0.16 mmol), and triethylamine(0.63 mL, 4.50 mmol) were added, this was degassed again under thenitrogen gas atmosphere, and stirred at 90° C. for 14 hours. Thereaction mixture was poured into ice water-2 mol/L hydrochloric acid,and extracted with ethyl acetate. The organic layer was washedsuccessively with an aqueous saturated sodium bicarbonate solution, andan aqueous saturated sodium chloride solution, dried over anhydroussodium sulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel chromatography, and the fractions eluted withethyl/n-hexane/chloroform=1/2/1 were collected, and crystallized withethyl acetate/n-hexane=1/3 to give a pale brown compound (8) (0.09 g,yield 21.0%). mp 174-176° C.

¹H NMR (CDCl₃) δ: 0.96 (t, J=7.5 Hz, 3H), 1.35-1.52 (m, 2H), 1.60-1.85(m, 2H), 3.23-3.40 (m, 8H), 3.77 (s, 3H), 3.93 (s, 3H), 3.99 (m, 1H),4.92 (d, J=9.6 Hz, 1H), 6.90 (d, J=9.0 Hz, 2H), 7.11 (d, J=2.7 Hz, 1H),7.16 (dd, J=2.4, 9.0 Hz, 1H), 7.48 (d, J=8.7 Hz. 2H), 7.53 (dd, J=1.8,8.7 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.70 (d, J=9.0 Hz, 1H), 7.95 (s,1H).

Step 5

To a solution of the compound (8) (0.08 g, 0.15 mmol) in dimethylsulfoxide (0.9 mL) was added a 1 mol/L aqueous sodium hydroxide solution(0.9 mL) at room temperature, and the mixture was stirred at 60° C. for14 hours. The reaction mixture was poured into ice water-5% aqueouscitric acid solution, and extracted with ethyl acetate. The organiclayer was washed with water, dried over anhydrous sodium sulfate, andconcentrated under reduced pressure. The residue was recrystallized fromacetone/n-hexane to give(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-pentanoicacid (I-1) (0.07 g, yield 90.0%). mp 187-190° C. (dec.)

¹H-NMR (DMSO-d₆) δ: 0.88 (t, J=7.5 Hz, 3H), 1.30-1.50 (m, 2H), 1.50-1.65(m, 2H), 3.05-3.45 (m, 8H), 3.69 (m, 1H), 3.89 (s, 3H), 7.00 (d, J=9.0Hz, 2H), 7.21 (dd, J=2.7, 9.0 Hz, 1H), 7.35 (d, J=2.7 Hz, 1H), 7.43 (d,J=8.7 Hz, 2H), 7.52 (dd, J=1.5, 8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H),7.85 (d, J=9.0 Hz, 1H), 7.91 (d, J=9.0 Hz, 1H), 8.04 (s, 1H), 12.78 (brs, 1H).

Synthesis of(R)-2-{4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-2)

Step 1

A solution of p-iodophenol (9) (10.0 g, 45.6 mmol) and potassiumcarbonate (9.42 g, 68.2 mmol) in dimethylformamide (100 mL) was degassedwell, and the atmosphere was replaced with a nitrogen gas. Then,2-bromomethylnaphthalene (10) (11.1 mg, 50.0 mmol) was added, and themixture was stirred at 70° C. for 1 hour. The reaction mixture wascooled to room temperature, and poured into ice-2 mol/L hydrochloricacid, and this was stirred for 5 minutes. The precipitated crystal wascollected by filtration, and washed with water to give a compound (3)(7.6 g, yield 46%). The mother liquor was extracted with ethyl acetate,and the organic layer was washed successively with water, and aqueoussaturated sodium chloride solution, dried over anhydrous sodium sulfate,and concentrated under reduced pressure. The residue was crystallizedwith tetrahydrofuran/water to obtain a compound (11) (8.6 g, yield 53%).(total amount 16.2 g, total yield 90%) mp 136-137° C.

¹H NMR (CDCl₃) δ: 5.20 (s, 2H), 6.80 (dd, J=2.1 Hz, 9.0 Hz, 2H),7.48-7.59 (m, 5H), 7.82-7.88 (m, 4H).

Step 2

A solution of a solution of the compound (11) (2.5 g, 9.7 mmol),1-t-butoxycarbonylpiperazine (12) (10.9 g, 58.3 mmol), sodium t-butoxide(13.1 g, 13.6 mmol) in toluene and N-methylpiperidone (7 mL) wasdegassed well, and the atmosphere was replaced with a nitrogen gas.Then, palladium acetate (0.11 g, 0.49 mmol) and tri-t-butylphosphine(0.47 mL, 1.94 mmol) were added, the atmosphere was replaced again witha nitrogen gas well, and the mixture was stirred at 120° C. for 5 hours.The reaction mixture was filtered through Celite and water was added tothe filtrate, which was extracted with ethyl acetate. The organic layerwas washed with aqueous saturated sodium chloride, dried over anhydroussodium sulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel chromatography, and the fractions eluted withethyl acetate/n-hexane=2/3 were collected, and concentrated underreduced pressure to give a compound (13). (2.6 g, yield 64%) mp 147-149°C.

¹H NMR (CDCl₃) δ: 1.48 (s, 9H), 3.01 (bs, 4H), 3.57 (bs, 4H), 5.19 (s,2H), 6.91-6.98 (m, 4H), 7.26-7.55 (m, 3H), 7.82-7.88 (m, 4H).

Step 3

To the compound (13) was added a 4 mol/L hydrochloric acid solution inethyl acetate (50 mL), and the mixture was stirred at room temperaturefor 30 minutes. The reaction mixture was concentrated under reducedpressure, and the residue was dissolved in methanol, and concentratedagain under reduced pressure. The residue was washed with ethyl acetate,and collected by filtration to obtain a compound (14). (2.4 g, 99%) mp200-201° C. ¹H NMR (DMSO-d₆) δ: 3.24 (bs, 8H), 5.22 (s, 2H), 4.98 (s,4H), 7.51-7.57 (m, 3H), 7.90-7.96 (m, 4H), 9.13 (bs, 2H).

Step 4

Compound (15) was prepared from compound (14) and compound (2) accordingto Step 1 of Example 1.

¹H NMR (CDCl₃) δ: 3.15 (t, J=4.8 Hz, 4H), 3.38 (t, J=4.8 Hz, 4H), 5.19(s, 2H), 6.88-6.97 (m, 4H), 7.18 (bs, 1H), 7.27 (bs, 1H), 7.47-7.53 (m,3H), 7.82-7.87 (m, 5H), 7.95 (s, 1H).

Compound (16) was prepared from compound (15) according to Step 2 ofExample 1.

¹H NMR (DMSO-d₆) δ: 3.16 (bs, 4H), 3.51 (bs, 4H), 3.89 (s, 3H), 5.21 (s,2H), 6.90-6.93 (m, 4H), 7.50-7.54 (m, 3H), 7.90-7.99 (m, 5H), 8.23 (t,J=1.8 Hz, 1H), 9.85 (s, 1H).

Step 6

Compound (18) was prepared from compound (16) and compound (17)according to Step 3 of Example 1.

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=6.8 Hz, 2H), 3.04 (bs, 4H), 3.14 (bs,4H), 3.65 (s, 3H), 3.83-3.95 (m, 1H), 5.21 (s, 2H), 6.90-6.97 (m, 4H),7.51-7.57 (m, 3H), 7.91-7.99 (m, 4H), 8.03 (d, J=8.8 Hz, 1H).

Step 7

(R)-2-{4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-2) was prepared from compound (18) according to Step 5 ofExample 1.

mp 167-171° C.

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.01 (bs, 4H), 3.14 (bs,4H), 3.81 (t, J=7.2 Hz, 1H), 5.21 (s, 2H), 6.91-6.98 (m, 4H), 7.51-7.57(m, 3H), 7.86-7.95 (m, 5H), 12.69 (bs, 1H).

According to the same manner as that described above, the followingcompounds were synthesized.

Synthesis of(S)-2-{4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-3)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=4.8 Hz, 3H), 3.05 (bs, 4H), 3.14 (bs,4H), 5.21 (s, 2H), 6.92-6.95 (m, 4H), 7.51-7.60 (m, 3H), 7.85-7.95 (m,5H)

Synthesis of(R)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-3-methyl-butanoicacid (I-4)

¹H NMR (DMSO-d₆) δ: 0.80-0.97 (m, 6H), 1.98 (m, 1H), 3.00-3.60 (m, 9H),3.89 (s, 3H), 7.00 (d, J=8.7 Hz, 2H), 7.21 (m, 1H), 7.35 (m, 1H), 7.43(d, J=8.7 Hz, 2H), 7.52 (m, 1H), 7.68-7.90 (m, 3H), 8.04 (s, 1H)

Synthesis of(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-3-methyl-butanoicacid (I-5)

¹H NMR (DMSO-d₆) δ: 0.91 (d, J=6.6 Hz, 3H), 0.93 (d, J=6.6 Hz, 3H), 1.98(m, 1H), 3.05-3.35 (m, 8H), 3.50 (m, 1H), 3.89 (s, 3H), 7.00 (d, J=9.0Hz, 2H), 7.21 (dd, J=2.4, 9.0 Hz, 1H), 7.35 (m, 1H), 7.43 (d, J=9.3 Hz,2H), 7.52 (m, 1H), 7.78-7.90 (m, 3H), 8.03 (s, 1H), 12.74 (br s, 1H)

Synthesis of(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-hexanoicacid (I-6)

¹H NMR (DMSO-d₆) δ: 0.86 (t, J=7.2 Hz, 3H), 1.20-1.44 (m, 4H), 1.50-1.72(m, 2H), 3.05-3.35 (m, 8H), 3.66 (m, 1H), 3.88 (s, 3H), 6.99 (d, J=9.0Hz, 2H), 7.20 (dd, J=2.4, 9.0 Hz, 1H), 7.34 (d, J=2.7 Hz, 1H), 7.42 (d,J=8.7 Hz, 2H), 7.51 (dd, J=1.8, 8.4 Hz, 1H), 7.81 (d, J=8.7 Hz, 1H),7.84 (d, J=9.3 Hz, 1H), 7.90 (d, J=8.1 Hz, 1H), 8.02 (s, 1H), 12.76 (brs, 1H)

Synthesis of(R)-2-{4-[4-(naphthalen-2-yloxymethyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-7)

¹H-NMR (DMSO-d₆) δ: 1.30 (d, J=8.8 Hz, 3H), 3.17-3.20 (m, 8H), 3.80 (bs,1H), 5.10 (s, 2H), 6.99 (d, J=7.7 Hz, 2H), 7.20 (d, J=9.6 Hz, 1H),7.34-7.47 (m, 5H), 7.78-7.83 (4H, m)

Synthesis of(R)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-8)

¹H-NMR (DMSO-d₆) δ: 1.30 (d, J=6.9 Hz, 3H), 3.05-3.40 (m, 8H), 3.80 (m,1H), 3.88 (s, 3H), 6.99 (d, J=8.7 Hz, 2H), 7.20 (dd, J=2.4, 9.0 Hz, 1H),7.34 (d, J=2.1 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.51 (dd, J=1.5, 8.1 Hz,1H), 7.81 (d, J=8.4 Hz, 1H), 7.83 (d, J=9.0 Hz, 1H), 7.91 (d, J=8.1 Hz,1H), 8.02 (s, 1H), 12.72 (br s, 1H)

Synthesis of(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-4-methyl-pentanoicacid (I-9)

¹H-NMR (DMSO-d₆) δ: 0.89 (d, J=6.3 Hz, 3H), 0.90 (d, J=6.6 Hz, 3H),1.35-1.60 (m, 2H), 1.74 (m, 1H), 3.05-3.40 (m, 8H), 3.70 (m, 1H), 3.89(s, 3H), 7.00 (d, J=9.0 Hz, 2H), 7.20 (dd, J=2.4, 9.0 Hz, 1H), 7.35 (d,J=3.0 Hz, 1H), 7.43 (d, J=9.0 Hz, 2H), 7.52 (m, 1H), 7.82 (d, J=8.7 Hz,1H), 7.84 (d, J=9.0 Hz, 1H), 7.95 (d, J=8.1 Hz, 1H), 8.03 (s, 1H), 12.76(br s, 1H)

Synthesis of(R)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl-3,6-dihydro-2H-pyridine-1-sulfonylamino}-propionicacid (I-10)

¹H-NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 2.50-2.60 (m, 2H), 3.20-3.30(m, 2H), 3.70-3.90 (m, 3H), 3.90 (s, 3H), 6.32 (m, 1H), 7.22 (dd, J=2.4,8.7 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.50-7.60 (m, 5H), 7.80-7.95 (m,3H), 8.10 (s, 1H), 12.71 (br s, 1H)

Synthesis of(R)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperidine-1-sulfonylamino}-propionicacid (I-11)

¹H-NMR (DMSO-d₆) δ: 1.31 (d, J=7.2 Hz, 3H), 1.55-1.75 (m, 2H), 1.75-1.92(m, 2H), 2.60-2.80 (m, 3H), 3.58-3.70 (m, 2H), 3.79 (m, 1H), 3.90 (s,3H), 7.22 (dd, J=2.7, 9.3 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.37 (d,J=2.4 Hz, 2H), 7.52 (d, J=8.4 Hz, 1H), 7.56 (m, 1H), 7.77 (d, J=7.8 Hz,1H), 7.85 (d, J=8.4 Hz, 1H), 7.87 (d, J=9.3 Hz, 1H), 8.09 (s, 1H), 12.75(br s, 1H)

Synthesis of(R)-2-{4-hydroxy-4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperidine-1-sulfonylamino}-propionicacid (I-12)

¹H-NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 1.60-1.75 (m, 2H), 1.85-2.02(m, 2H), 2.95-3.15 (m, 2H), 3.30-3.50 (m, 2H), 3.79 (m, 1H), 3.89 (s,3H), 5.18 (s, 1H), 7.21 (dd, J=2.7, 8.7 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H),7.48-7.58 (m, 5H), 7.74 (d, J=7.2 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.86(d, J=8.7 Hz, 1H), 8.08 (s, 1H), 12.69 (br s, 1H)

Synthesis of(S)-2-{4-[4-(((E)-naphthalen-2-yl-vinyl)-phenyl]-piperazine-1-sulfonylamino}-pentanoicacid (I-13)

¹H-NMR (DMSO-d₆) δ: 0.89 (t, J=6.8 Hz, 3H), 1.32-1.44 (m, 2H), 1.54-1.63(m, 2H), 3.16-3.33 (m, 8H), 3.66-3.74 (m, 1H), 7.00 (d, J=7.2 Hz. 2H),7.23 (d, J=16.8 Hz, 1H), 7.32 (d, J=16.8 Hz, 1H), 7.43-7.54 (m, 4H),7.82-7.88 (m, 5H), 7.94 (s, 1H), 12.70 (br s, 1H)

Synthesis of(S)-2-{4-[4-(2-naphthalen-2-yl-ethyl)-phenyl]-piperazine-1-sulfonylamino}-pentanoicacid (I-14)

¹H-NMR (DMSO-d₆) δ: 0.88 (t, J=6.8 Hz. 3H), 1.32-1.44 (m, 2H), 1.54-1.63(m, 2H), 2.87-2.91 (m, 2H), 2.96-3.02 (m, 2H), 3.11 (s, 4H), 3.32 (s,4H), 3.63-3.71 (m, 1H), 6.86 (d, J=7.2 Hz, 2H), 7.11 (d, J=7.2 Hz, 2H),7.41-7.48 (m, 3H), 7.70 (s, 1H), 7.81-7.86 (m, 4H), 12.70 (br s, 1H).

Synthesis of(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-15)

¹H-NMR (DMSO-d₆) δ: 1.20 (d, J=6.3 Hz, 3H), 3.03 (bs, 4H), 3.16 (bs,4H), 3.88 (s, 3H), 5.14 (s, 2H), 6.89-6.93 (m, 4H), 7.17 (d, J=8.8 Hz,1H), 7.32 (s, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.92(s, 1H).

Synthesis of(R)-2-{4-[4-(6-methoxy-naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-16)

¹H-NMR (DMSO-d₆) δ: 1.20 (d, J=6.3 Hz, 3H), 3.03 (bs, 4H), 3.16 (bs,4H), 3.88 (s, 3H), 5.14 (s, 2H), 6.93 (d, J=7.3 Hz, 4H), 7.17 (d, J=8.8Hz, 1H), 7.32 (s, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.83 (d, J=8.8 Hz, 2H),7.87 (s, 1H).

Synthesis of(S)-2-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperidine-1-sulfonylamino}-pentanoicacid (I-17)

¹H-NMR (DMSO-d₆) δ: 0.90 (d, J=7.2 Hz, 3H), 1.30-1.74 (m, 6H), 1.74-1.92(m, 2H), 2.56-2.80 (m, 3H), 3.58-3.73 (m, 3H), 3.89 (s, 3H), 7.22 (dd,J=2.4, 8.7 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.37 (d, J=2.1 Hz, 2H),7.49-7.58 (m, 3H), 7.77 (d, J=9.0 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.87(d, J=8.7 Hz, 1H), 8.09 (s, 1H), 12.73 (br s, 1H).

Synthesis of(I-2-{4-fluoro-4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperidine-1-sulfonylamino}-propionicacid (I-18)

¹H-NMR (DMSO-d₆) δ: 1.31 (d, J=6.9 Hz, 3H), 1.90-2.30 (m, 4H), 2.85-3.05(m, 2H), 3.50-3.63 (m, 2H), 3.83 (m, 1H), 3.89 (s, 3H), 7.22 (dd, J=2.4,9.0 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H), 7.49 (d, J=8.4 Hz, 2H), 7.56 (m,1H), 7.61 (d, J=8.4 Hz, 1H), 7.80-7.95 (m, 3H), 8.10 (s, 1H), 12.83 (brs, 1H).

Synthesis of(I-2-{4-[4-(6-methoxy-naphthalen-2-ylmethoxy)-phenyl]-piperidine-1-sulfonylamino}-propionicacid (I-19)

¹H-NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 2H), 1.57 (t, J=8.8 Hz, 2H), 1.78(t, J=11.2 Hz, 2H), 2.62-2.73 (m, 2H), 3.60 (bs, 2H), 3.79 (t, J=7.2 Hz1H), 3.88 (s, 3H), 5.19 (s, 2H), 6.98 (d, J=8.6 Hz, 2H), 7.16 (t, J=7.1Hz, 3H), 7.32 (s, 1H), 7.52 (d, J=9.1 Hz, 1H), 7.71 (d, J=9.1 Hz, 1H),7.83 (d, J=8.8 Hz, 2H), 7.89 (s, 1H).

Synthesis of(S)-2-(4-{4-[2-(6-methoxy-naphthalen-2-yl)-ethyl]-phenyl}-piperidine-1-sulfonylamino]-pentanoicacid (I-20)

¹H NMR (DMSO-d₆) δ: 0.90 (d, J=6.6 Hz, 3H), 1.38-1.40 (m, 2H), 1.58-1.61(m, 4H), 1.75-1.79 (m, 2H), 2.65-2.72 (m, 2H), 2.95 (d, J=12.1 Hz, 4H).3.61-3.63 (m, 3H), 3.83 (s, 3H), 7.14-7.17 (m, 5H), 7.27 (s, 1H), 7.38(d. J=6.6 Hz, 1H), 7.63 (s, 1H), 7.71 (t, J=9.7 Hz, 3H).

Synthesis of(S)-2-(4-{4-[(E)-2-(6-methoxy-naphthalen-2-yl)-vinyl]-phenyl}-piperazine-1-sulfonylamino}-propionicacid (I-21)

¹H NMR (DMSO-d₆) δ: 1.27 (d, J=6.8 Hz, 3H), 3.38-3.28 (m, 8H), 3.65 (bs,1H), 3.86 (s, 3H), 6.98 (d, J=8.4 Hz, 2H), 7.14-7.16 (m, 1H), 7.20 (d,J=9.6 Hz, 2H), 7.14-7.16 (m, 1H), 7.20 (d, J=9.6 Hz, 2H), 7.29 (s, 1H),7.50 (d, J=8.4 Hz, 2H), 7.73-7.80 (m, 3H), 7.87 (s, 1H).

Synthesis of(S)-2-(4-{4-[2-(6-methoxy-naphthalen-2-yl)-ethyl]-phenyl)-piperazine-1-sulfonylamino}-propionicacid (I-22)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=7.6 Hz, 3H), 2.86-2.91 (m, 2H), 2.93-2.95(m, 2H), 3.12 (bs, 8H), 3.80-3.82 (bs, 1H), 3.85 (s, 3H), 6.86 (d, J=8.4Hz, 2H), 7.09 (bs, 3H), 7.26 (s, 1H), 7.35 (d, J=7.2 Hz, 1H), 7.61 (s,1H), 7.72 (d, J=9.2 Hz, 2H), 7.83-7.84 (m, 1H).

Synthesis of(R)-2-{4-methoxy-4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-piperidine-1-sulfonylamino}-propionicacid (I-23)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=6.9 Hz, 3H), 1.80-2.15 (m, 4H), 2.91 (s,3H), 2.90-3.05 (m, 2H), 3.78 (m, 1H), 3.90 (s, 3H), 7.23 (dd, J=2.7, 9.3Hz, 1H), 7.38 (d, J=2.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.56 (dd,J=1.8, 8.7 Hz, 1H), 7.60 (d, J=8.4 Hz, 2H), 7.79 (m, 1H), 7.86 (d, J=8.4Hz, 1H), 7.88 (d, J=8.7 Hz, 1H), 8.11 (s, 1H)

Synthesis of(S)-2-(4-{4-[(A)-2-(6-methoxy-naphthalen-2-yl)-vinyl]-phenyl)-piperidine-1-sulfonylamino}-pentanoicacid (I-24)

¹H NMR (DMSO-d₆) δ: 0.88 (t, J=7.2 Hz, 3H), 1.38 (t, J=7.2 Hz, 2H),1.58-1.62 (m, 4H), 2.64-2.76 (m, 3H), 3.61-3.64 (m, 2H), 3.69 (s, 3H),3.77-3.81 (m, 1H), 7.27 (d, J=8.0 Hz, 2H), 7.38 (s, 2H), 7.47-7.52 (m,2H), 7.59 (d, J=6.8 Hz, 2H), 7.85-7.92 (m, 4H), 8.00 (bs, 1H).

Synthesis of(S)-2-{4-[4-((E)-2-naphthalen-2-yl-vinyl)-phenyl-piperidine-1-sulfonylamino)-pentanoicacid (I-25)

¹H NMR (DMSO-d₆) δ: 0.90 (d, J=7.6 Hz, 3H), 1.36-1.40 (m, 2H), 1.58-1.68(m, 4H), 1.81-1.84 (m, 2H), 2.64-2.74 (m, 3H), 3.64-3.66 (m, 2H), 7.27(bs, 2H), 7.38 (d, J=4.4 Hz, 2H), 7.46-7.50 (m, 2H), 7.56-7.60 (m, 2H),7.69-7.72 (m, 1H), 7.86-7.89 (m, 4H), 7.99-8.01 (m, 1H).

Synthesis of(R)-2-{4-[4-((E)-2-naphthalen-2-yl-vinyl)-phenyl]-piperidine-1-sulfonylamino)-propionicacid (I-26)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=6.8 Hz, 3H), 1.59-1.66 (m, 2H), 1.84-1.87(m, 2H), 2.57-2.77 (m, 4H), 3.65 (bs, 2H), 3.79 (bs, 1H), 7.28 (d, J=7.2Hz, 2H), 7.38 (s, 2H), 7.49-7.51 (m, 2H), 7.68-7.72 (m, 1H), 7.85-7.90(m, 4H), 7.99 (bs, 1H).

Synthesis of(R)-2-{4-[4-(6-ethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-27)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 1.40 (t, J=6.9 Hz, 3H),3.05-3.40 (m, 8H), 3.81 (m, 1H), 4.16 (q, J=6.9 Hz, 2H), 7.00 (d, J=9.0Hz, 2H), 7.19 (dd, J=2.7, 9.3 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 7.43 (d,J=8.7 Hz, 2H), 7.51 (dd, J=1.5, 8.4 Hz, 1H), 7.76-7.88 (m, 2H), 7.93 (d,J=9.0 Hz, 1H), 8.03 (s, 1H), 12.72 (br s, 1H).

Synthesis of(S)-2-{4-[4-(6-ethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-pentanoicacid (I-28)

¹H NMR (DMSO-d₆) δ: 0.88 (t, J=7.2 Hz, 3H), 1.40 (t, J=7.2 Hz, 3H),1.28-1.48 (m, 2H), 1.50-1.68 (m, 2H), 3.05-3.40 (m, 8H), 3.68 (m, 1H),4.15 (q, J=6.9 Hz, 2H), 6.99 (d, J=9.0 Hz, 2H), 7.18 (dd, J=2.4, 9.0 Hz,1H), 7.32 (d, J=2.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.50 (dd, J=1.5,8.7 Hz, 1H), 7.76-7.86 (m, 2H), 7.91 (d, J=9.0 Hz, 1H), 8.02 (s, 1H),12.71 (br s, 1H).

Synthesis of(R)-2-{4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperidine-1-sulfonylamino)-propionicacid (I-29)

¹H NMR (DMSO-d₆) δ: 1.29-1.31 (m, 3H), 1.57-1.59 (m, 2H), 1.75-1.78 (m,2H), 2.65-2.77 (m, 2H), 3.60 (bs, 2H), 3.78 (bs, 1H), 6.99 (d, J=6.8 Hz,2H), 7.15-7.17 (m, 2H), 7.51-7.58 (m, 3H), 7.69-7.74 (m, 4H).

Synthesis of(S)-2-{4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperidine-1-sulfonylamino)-pentanoicacid (I-30)

¹H NMR (DMSO-d₆) δ: 0.89 (t, J=7.2 Hz, 3H), 1.37-1.40 (m, 2H), 1.53-1.58(m, 3H), 1.74-1.81 (m, 2H), 2.60-2.72 (m, 2H), 3.59-3.69 (m, 2H), 5.25(s, 2H), 6.99 (d, J=7.2 Hz, 2H), 7.15 (d, J=7.2 Hz, 2H), 7.51-7.58 (m,3H), 7.68 (d, J=5.6 Hz, 1H), 7.92-7.97 (m, 4H).

Synthesis of(S)-2-{4-[4-(6-methoxymethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-31)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.05-3.40 (m, 8H), 3.42 (s,3H), 3.80 (m, 1H), 5.33 (s, 2H), 7.00 (d, J=8.7 Hz, 2H), 7.28 (dd,J=2.1, 8.4 Hz, 1H), 7.36-7.56 (m, 4H), 7.81 (d, J=8.7 Hz, 1H), 7.87 (d,J=9.0 Hz, 1H), 7.92 (m, 1H), 8.04 (s, 1H), 12.70 (br s, 1H).

Synthesis of(R)-2-{4-[4-(6-cyclopropylmethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-32)

¹H NMR (DMSO-d₆) δ: 0.32-0.42 (m, 2H), 0.56-0.66 (m, 2H), 1.30 (d, J=7.2Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m, 1H), 3.95 (d, J=6.9 Hz, 2H), 7.00(d, J=9.0 Hz, 2H), 7.22 (dd, J=2.1, 8.7 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H),7.43 (d, J=9.0 Hz, 2H), 7.50 (dd, J=1.2, 8.7 Hz, 1H), 7.79 (d, J=8.4 Hz,1H), 7.84 (d, J=9.3 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 8.02 (m, 1H), 12.72(br s, 1H).

Synthesis of(R)-2-{4-[4-(6-hydroxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-33)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=6.9 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m,1H), 7.00 (d, J=8.7 Hz, 2H), 7.08-7.16 (m, 2H), 7.38-7.48 (m, 3H), 7.69(d, J=9.0 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.97(s, 1H), 9.94 (s, 1H), 12.75 (br s, 1H).

Synthesis of(R)-2-{4-[4-(naphthalen-2-ylmethylsulfanyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-34)

¹H NMR (DMSO-d₆) δ: 1.28 (d, J=6.8 Hz, 3H), 3.32 (bs, 8H), 3.79 (bs,1H), 4.24 (s, 2H), 6.86 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H),7.46-7.47 (m, 3H), 7.70 (s, 1H), 7.79-7.85 (m, 4H).

Synthesis of(R)-2-{4-[4-(naphthalen-2-ylmethanesulfinyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-35)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=6.8 Hz, 3H), 3.14-3.17 (m, 4H), 3.79-3.83(m, 1H), 4.20 (d, J=8.4 Hz, 1H), 4.33 (d, J=8.4 Hz, 1H), 7.06 (d, J=8.8Hz, 2H), 7.24 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.47-7.52 (m,2H), 7.65 (s, 1H), 7.81 (d, J=7.2 Hz, 2H), 7.89 (bs, 2H).

Synthesis of(R)-2-{4-[4-(6-hydroxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-36)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=6.8 Hz, 3H), 1.60-1.65 (m, 2H), 1.81-1.84(m, 2H), 2.62-2.76 (m, 3H), 3.64 (bs, 2H), 3.80 (bs, 1H), 7.14 (d, J=8.0Hz, 2H), 7.31 (d, J=8.0 Hz, 2H), 7.46-7.52 (m, 3H), 7.71 (d, J=8.8 Hz,2H), 7.79 (d, J=8.8 Hz, 1H), 8.02 (bs, 1H).

Synthesis of(R)-2-{4-[4-(naphthalen-2-ylmethanesulfonyl)-phenyl]-4-oxy-piperazine-1-sulfonylamino)-propionicacid (I-37)

¹H NMR (DMSO-d₆) δ: 1.28 (d, J=7.2 Hz, 3H), 3.24 (d, J=9.2 Hz, 2H), 3.53(t, J=13.6 Hz, 2H), 3.70-3.82 (m, 3H), 4.00-4.06 (m, 2H), 4.94 (s, 2H),7.31 (d, J=8.4 Hz, 2H), 7.53 (d, J=4.0 Hz, 2H), 7.69 (s, 1H), 7.82-7.92(m, 6H), 8.38 (d, J=8.4 Hz, 2H).

Synthesis of(R)-2-[4-[4-(naphthalen-2-ylmethanesulfonyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-38)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.09-3.17 (m, 4H), 3.37-3.39(m, 4H), 3.77-3.83 (m, 1H), 4.70 (s, 2H), 7.02 (d, J=8.8 Hz, 2H), 7.27(d, J=8.8 Hz, 1H), 7.47-7.53 (m, 4H), 7.69 (bs, 1H), 7.82 (d, J=8.0 Hz,2H), 7.88-7.93 (m, 4H).

Synthesis of(R)-2-(4-{4-[6-(2-hydroxy-ethoxy)-naphthalen-2-ylethynyl]-phenyl}-piperazine-1-sulfonylamino)-propionicacid (I-39)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.10-3.40 (m, 8H), 3.74-3.86(m, 3H), 4.12 (t, J=5.4 Hz, 2H), 4.94 (m, 1H), 7.10 (d, J=9.0 Hz, 2H),7.22 (dd, J=2.4, 9.3 Hz, 1H), 7.35 (d, J=2.4 Hz, 1H), 7.43 (d, J=8.7 Hz,2H), 7.51 (d, J=8.7 Hz, 1H), 7.79-7.88 (m, 2H), 7.92 (d, J=7.2 Hz, 1H),8.03 (s, 1H), 12.77 (br s, 1H).

Synthesis of(R)-2-{(R)-3-methyl-4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-40)

¹H NMR (DMSO-d₆) δ: 0.85 (d, J=5.6 Hz, 3H), 1.32 (d, J=6.8 Hz, 3H),2.96-2.98 (m, 2H), 3.08 (bs, 3H), 3.66 (bs, 1H), 3.82 (bs, 1H), 5.20 (s,2H), 6.94 (dd, J=8.0 Hz, 9.2 Hz, 4H), 7.52-7.58 (m, 3H), 7.79 (bs, 1H),7.92-7.94 (m, 4H).

Synthesis of(R)-2-{(2R,6S)-2,6-dimethyl-4-[4-(naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-41)

¹H NMR (DMSO-d₆) δ: 1.27 (d, J=7.2 Hz, 3H), 1.40 (t, J=6.4 Hz, 6H),2.97-2.71 (m, 2H), 3.62-3.66 (m, 1H), 3.91 (bs, 2H), 5.22 (s, 2H), 6.93(dd, J=8.8 Hz, 9.2 Hz, 4H), 7.51-7.58 (m, 4H), 7.91-7.96 (m, 4H).

Synthesis of(R)-2-(4-{4-[4-(naphthalene-2-carbonyl)-amino]-phenyl}-piperazine-1-sulfonylamino)-propionicacid (I-42)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=6.8 Hz, 3H), 3.18 (s, 8H), 3.80-3.85 (m,1H), 6.99 (d, J=8.0 Hz, 2H), 7.61-7.71 (m, 4H), 7.91 (d, J=8.4 Hz, 1H),7.99-8.09 (m, 4H), 8.56 (s, 1H), 10.27 (s, 1H), 12.73 (br s, 1H).

Synthesis of(R)-2-{4-[4-(methyl-naphthalen-2-ylmethyl-amino)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-43)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=6.8 Hz, 3H), 2.96 (s, 7H), 3.12 (s, 4H),3.77-3.83 (m, 1H), 4.70 (s, 2H), 6.72 (d, J=7.6 Hz, 2H), 6.83 (d, J=7.6Hz, 2H), 7.38 (d, J=8.0 Hz, 1H), 7.46-7.48 (m, 2H), 7.70 (s, 1H),7.82-7.87 (m, 4H), 12.69 (br s, 1H).

Synthesis of(R)-2-(4-{4-[4-(naphthalen-2-ylmethyl)-amino]-phenyl}-piperazine-1-sulfonylamino)-propionicacid (I-44)

¹H NMR (DMSO-d₆) δ: 1.28 (d, J=6.8 Hz, 3H), 2.93 (s, 4H), 3.10 (s, 4H),3.76-3.80 (m, 1H), 4.38 (s, 2H), 6.56 (d, J=7.6 Hz, 2H), 6.73 (d, J=7.6Hz, 2H), 7.46-7.53 (m, 3H), 7.81-7.87 (m, 5H), 12.61 (br s, 1H).

Synthesis of(R)-2-(4-{4-[4-(6-methoxy-naphthalen-2-ylmethyl)-amino]-phenyl}-piperazine-1-sulfonylamino)-propionicacid (I-45)

¹H NMR (DMSO-d₆) δ: 1.28 (d, J=6.8 Hz, 3H), 2.92 (s, 4H), 3.10 (s, 4H),3.76-3.80 (m, 1H), 3.85 (s, 3H), 4.32 (s, 2H), 6.54 (d, J=7.6 Hz, 2H),6.72 (d, J=7.6 Hz, 2H), 7.12 (d, J=8.6 Hz, 1H), 7.28 (s, 1H), 7.46 (d,J=8.6 Hz, 1H), 7.76 (s, 3H), 7.82 (d, J=7.6 Hz, 1H), 12.12 (br s, 1H).

Synthesis of(I-2-(4-{4-[4-(6-carboxymethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino)-propionicacid (I-46)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=6.6 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m,1H), 4.82 (s, 2H), 7.00 (d, J=8.4 Hz, 2H), 7.20-7.32 (m, 2H), 7.43 (d,J=8.1 Hz, 2H), 7.51 (d, J=8.7 Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.87 (d,J=9.3 Hz, 1H), 7.93 (m, 1H), 8.04 (s, 1H), 12.40-13.40 (m, 2H).

Synthesis of (R)-2-(4-{4-[4(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-2-methyl-piperazine-1-sulfonylamino)-propionicacid (I-47)

¹H NMR (DMSO-d₆) δ: 1.22-1.32 (m, 6H), 2.65-3.30 (m, 4H), 3.55-3.80 (m,3H), 3.89 (s, 3H), 3.95 (m, 1H), 6.97 (d, J=9.0 Hz, 2H), 7.21 (dd,J=2.7, 9.0 Hz, 1H), 7.35 (d, J=2.1 Hz, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.52(dd, J=1.5, 8.7 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.84 (d, J=9.3 Hz, 1H),7.92 (m, 1H), 8.03 (s, 1H), 12.72 (br s, 1H).

Synthesis of(R)-2-(4-{4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl]-[1,4]diazepane-1-sulfonylamino)-propionicacid (I-48)

¹H NMR (DMSO-d₆) δ: 1.25 (d, J=7.1 Hz, 3H), 3.22-3.61 (m, 11H), 3.93 (s,3H), 6.81-6.84 (m, 2H), 7.23-7.26 (m, 1H), 7.39-7.42 (m, 3H), 7.52-7.64(m, 2H), 7.81-7.91 (m, 2H), 8.03 (br s, 1H).

Synthesis of(S)-2-(4-{4-[(E)-2-(6-methoxymethoxy-naphthalen-2-yl)-vinyl]-phenyl}-piperazine-1-sulfonylamino)-pentanoicacid (I-49)

¹H NMR (DMSO-d₆) δ: 0.89 (t, J=6.8 Hz, 3H), 1.33-1.43 (m, 2H), 1.55-1.62(m, 2H), 3.14-3.26 (m, 8H), 3.44-3.71 (m, 4H), 5.32 (s, 2H), 7.00 (d,J=8.4 Hz, 2H), 7.17-7.28 (m, 3H), 7.42 (s, 1H), 7.51 (d, J=8.4 Hz, 2H),7.78 (s, 2H), 7.82-7.92 (m, 3H).

Synthesis of(S)-2-(4-(4-[(E)-2-(6-hydroxy-naphthalen-2-yl)-vinyl]-phenyl}-piperazine-1-sulfonylamino)-pentanoicacid (I-50)

¹H NMR (DMSO-d₆) δ: 0.89 (t, J=6.8 Hz, 3H), 1.33-1.43 (m, 2H), 1.55-1.62(m, 2H), 3.14-3.26 (m, 8H), 3.67-3.71 (m, 1H), 6.98 (d, J=8.0 Hz, 2H),7.05-7.23 (m, 4H), 7.49 (d, J=8.4 Hz, 2H), 7.64-7.73 (m, 3H) 7.81 (s,1H), 7.90 (d, J=8.8 Hz, 1H), 9.75 (s, 1H), 12.73 (s, br s, 1H).

Synthesis of(S)-2-(4-(4-[(E)-2-(6-methoxy-naphthalen-2-yl)-vinyl]-phenyl)-[1,4]diazepane-1-sulfonylamino)-pentanoicacid (I-51)

¹H NMR (DMSO-d₆) δ: 0.84-0.87 (m, 3H), 1.25-1.35 (m, 3H), 1.48-1.58 (m,2H), 1.84-1.94 (m, 2H), 3.10-3.63 (m, 11H), 3.89 (s, 3H), 6.77-6.80 (m,2H), 7.18-7.22 (m, 1H), 7.35-7.38 (m, 3H), 7.49-7.51 (m, 1H), 7.60-7.63(m, 1H), 7.80-7.85 (m, 2H), 8.00 (br s, 1H).

Synthesis of(R)-2-{4-[4-(6-ethoxy-naphthalen-2-ylmethoxy)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-52)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=8.0 Hz, 3H), 1.39 (t, J=8.0 Hz, 3H),3.04-3.17 (m, 8H), 3.77-3.81 (m, 1H), 4.14 (dd, J=8.0 Hz, 12.0 Hz, 2H),5.14 (s, 2H), 6.89-6.95 (m, 4H), 7.15 (d, J=8.4 Hz, 1H), 7.30 (s, 1H),7.49 (d, J=8.0 Hz, 1H), 7.79-7.86 (m, 4H).

Synthesis of(R)-2-{(S)-4-[4-(6-methoxy-naphthalen-2-ylethynyl)-phenyl-3-methylpiperazine-1-sulfonylamino}-propionicacid (I-53)

¹H NMR (DMSO-d₆) δ: 1.02 (d, J=6.3 Hz, 3H), 1.28-1.35 (m, 3H), 2.60-3.10(m, 4H), 3.45-3.60 (m, 2H), 3.85 (m, 1H), 3.89 (s, 3H), 4.25 (m, 1H),6.94 (d, J=8.7 Hz, 2H), 7.21 (dd, J=2.7, 9.0 Hz, 1H), 7.35 (d, J=2.1 Hz,1H), 7.42 (d, J=8.7 Hz, 2H), 7.52 (d, J=9.0 Hz, 1H), 7.78-7.88 (m, 2H),8.00 (m, 1H), 8.03 (s, 1H), 12.70 (br s, 1H).

Synthesis of(R)-2-(4-{4-[6-((A)-3-hydroxy-buta-1,3-dienyl)-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-55)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.13-3.33 (m, 8H), 3.81 (brs, 1H), 6.69 (d, J=15.9 Hz, 1H), 7.02 (d, J=8.7 Hz, 2H), 7.46 (d, J=8.7Hz, 2H), 7.59-7.62 (m, 1H), 7.74 (d, J=15.9 Hz, 1H), 7.90-7.97 (m, 4H),8.13 (s, 1H), 8.20 (s, 1H), 12.6 (br s, 1H).

Synthesis of(R)-2-{4-[4-(6-acetylamino-naphthalen-2-ylethynyl)-phenyl)-]-piperazine-1-sulfonylamino}-propionicacid (I-56)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=7.2 Hz, 3H), 2.12 (s, 3H), 3.14-3.22 (m,4H), 3.79-3.84 (m, 1H), 7.00 (d, J=8.8 Hz, 2H), 7.44 (d, J=8.4 Hz, 2H),7.49-7.65 (m, 3H), 7.80-7.92 (m, 2H), 8.02 (s, 1H), 8.30 (s, 1H).

Synthesis of(R)-2-{4-[4-(6-amino-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-57)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 2.54 (s, 2H), 3.15-3.17 (m,4H), 3.80-3.84 (m, 1H), 6.95-7.00 (m, 3H), 7.40 (d, J=8.4 Hz, 2H), 7.49(d, J=8.4 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.81 (bs, 1H), 7.90 (d, J=8.4Hz, 1H).

Synthesis of(R)-2-[4-(4-{2-[6-(2-carboxy-ethyl)-naphthalen-2-yl]ethyl)-phenyl)-piperazine-1-sulfonylamino]-propionicacid (I-58)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=7.2 Hz, 3H), 2.59-2.65 (m, 2H), 2.84-2.91(m, 2H), 2.94-2.99 (m, 4H), 3.07-3.17 (m, 8H), 3.79 (br s, 1H), 6.86 (d,J=8.4 Hz, 2H), 7.10 (d, J=8.4 Hz, 2H), 7.34-7.40 (m, 2H), 7.63-7.67 (m,2H), 7.71-7.76 (m, 2H), 7.86 (br s, 1H).

Synthesis of(R)-2-{4-[4-(6-dimethylcarbamoylmethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-59)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=6.8 Hz, 3H), 2.87 (s, 3H), 3.05 (s, 3H),3.13-3.22 (m, 4H), 3.25-3.31 (m, 4H), 3.78-3.82 (m, 1H), 4.94 (s, 2H),7.00 (d, J=8.4 Hz, 2H), 7.23-7.29 (m, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.51(d, J=8.4 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.84-7.91 (m, 2H), 8.03 (s,1H).

Synthesis of6-{4-[4-((R)-1-carboxy-ethylsulfamoyl)-piperazin-1-yl]-phenylethynyl}-naphthalene-2-carboxylicacid (I-60)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.5 Hz, 3H), 3.05-3.40 (m, 8H), 3.81 (m,1H), 7.02 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.4 Hz,1H), 7.92 (m, 1H), 8.01 (s, 2H), 8.14 (d, J=9.0 Hz, 1H), 8.19 (s, 1H),8.61 (s, 1H), 13.00 (m, 1H).

Synthesis of(R)-2-[4-(4-naphthalen-2-ylethynyl-phenyl)-piperazine-1-sulfonylamino]-propionicacid (I-61)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.08-3.35 (m, 8H), 3.81 (m,1H), 7.02 (d, J=9.0 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 7.52-7.60 (m, 3H),7.88-7.98 (m, 4H), 8.12 (s, 1H), 12.69 (br s, 1H).

Synthesis of(R)-2-{4-[4-(6-methanesulfonylamino-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-62)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=7.2 Hz, 3H), 3.09 (s, 3H), 3.16-3.20 (m,4H), 3.30 (bs, 4H), 7.01 (d, J=8.8 Hz, 2H), 7.41-7.45 (m, 3H), 7.54 (d,J=8.4 Hz, 1H), 7.69 (s, 1H), 7.84-7.92 (m, 3H), 8.05 (s, 1H).

Synthesis of(S)-2-(4-{4-[(E)-2-(6-carboxymethoxy-naphthalen-2-yl)-vinyl]-phenyl}-piperazine-1-sulfonylamino]-pentanoicacid (I-63)

¹H NMR (DMSO-d₆) δ: 0.84-0.91 (m, 3H), 1.34-1.44 (m, 2H), 1.57-1.64 (m,2H), 3.16-3.24 (m, 8H), 3.70-3.73 (m, 1H), 4.80 (s, 2H), 7.15-7.25 (m,4H), 7.50 (d, J=8.4 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 7.77-7.88 (m, 5H).

Synthesis of(R)-2-(4-{4-[6-(2-carboxy-ethyl)-naphthalen-2-ylethynyl]-phenyl}-piperazine-1-sulfonylamino]-propionicacid (I-64)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=7.0 Hz, 3H), 2.64 (t, J=7.5 Hz, 2H), 2.99(t, J=7.5 Hz, 2H), 3.10-3.42 (m, 8H), 3.79 (br s, 1H), 6.99 (d, J=8.7Hz, 2H), 7.41-7.47 (m, 3H), 7.51 (d, J=7.6 Hz, 1H), 7.72 (s, 1H), 7.83(d, J=8.7 Hz, 2H), 7.88 (br s, 1H), 8.05 (s, 1H).

Synthesis of(R)-2-(4-{4-[6-(methoxyimino-methyl)-naphthalen-2-ylethynyl]-phenyl)-piperazine-1-sulfonylamino]-propionicacid (I-66)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.10-3.40 (m, 8H), 3.80 (m,1H), 3.95 (s, 3H), 7.02 (d, J=9.0 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H), 7.61(d, J=8.7 Hz, 1H), 7.80-8.20 (m, 4H), 8.10 (d, J=12.6 Hz, 1H), 8.38 (s,1H).

Synthesis of(T-2-{4-[4-(6-morpholin-4-yl-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-67)

¹H NMR (DMSO-d₆) δ: 1.29 (d, J=7.2 Hz, 3H), 3.15-3.20 (m, 4H), 3.75-3.79(m, 4H), 6.99 (d, J=8.4 Hz, 2H), 7.19 (s, 1H), 7.41-7.48 (m, 4H), 7.71(d, J=8.0 Hz, 2H), 7.94 (s, 1H).

Synthesis of(I-2-{4-[4-(6-dimethylcarbamoyl-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-68)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 2.98 (s, 3H), 3.04 (s, 3H),3.12-3.40 (m, 8H), 3.80 (br s, 1H), 7.02 (d, J=8.9 Hz, 2H), 7.46 (d,J=8.9 Hz, 2H), 7.53-7.58 (m, 1H), 7.60-7.66 (m, 1H), 7.90 (br s, 1H),7.96-8.02 (m, 3H), 8.16 (s, 1H).

Synthesis of(R)-2-{4-[4-(4-cyano-6-methoxymethoxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-83)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=6.8 Hz, 3H), 3.15-3.21 (m, 4H), 3.46 (s,3H), 3.82 (bs, 1H), 5.42 (s, 2H), 7.02 (d, J=8.8 Hz, 2H), 7.45-7.48 (m,3H), 7.45-7.48 (m, 3H), 7.56 (s, 1H), 7.91 (bs, 1H), 8.08 (d, J=8.8,1H), 8.20 (s, 1H), 8.41 (s, 1H).

Synthesis of(T-2-{4-[4-(4-cyano-6-hydroxy-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-84)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=6.8 Hz, 3H), 3.14-3.17 (m, 4H), 3.82 (bs,1H), 7.01 (d, J=7.6 Hz, 2H) 7.28 (d, J=8.0 Hz, 1H), 7.36 (s, 1H), 7.44(d, J=7.6 Hz, 2H), 7.99 (d, J=8.8, 1H), 8.12 (s, 1H), 8.34 (s, 1H).

Synthesis of3-{4-[4-((R)-1-carboxy-ethylsulfamoyl)-piperazin-1-yl]-phenylethynyl}-naphthalene-2-carboxylicacid (I-97)

¹H NMR (DMSO-d₆) δ: 1.32 (d, J=6.8 Hz, 3H), 3.18 (bs, 8H), 3.81-3.85 (m,1H), 7.03 (d, J=8.0 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.61-7.69 (m, 2H),7.91 (d, J=8.0 Hz, 1H), 7.99 (d, J=8.0 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H),8.22 (s, 1H), 8.52 (s, 1H).

Synthesis of(R)-2-{4-[4-(6-acetyl-naphthalen-2-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-116)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 2.71 (s, 3H), 3.05-3.40 (m,8H), 3.81 (m, 1H), 7.03 (d, J=9.0 Hz, 2H), 7.47 (d, J=9.0 Hz, 2H), 7.67(d, J=1.5, 8.4 Hz, 1H), 7.92 (m, 1H), 7.96-8.06 (m, 2H), 8.15 (d, J=8.4Hz, 1H), 8.19 (s, 1H), 8.68 (s, 1H), 12.77 (br s, 1H).

Synthesis of(A)-2-{4-[4-(9H-carbazol-3-ylethynyl)-phenyl]-piperazine-1-sulfonylamino}-propionicacid (I-129)

¹H NMR (DMSO-d₆) δ: 1.30 (d, J=7.2 Hz, 3H), 3.15-3.21 (m, 4H), 3.82 (bs,1H), 6.99 (d, J=8.8 Hz, 2H), 7.19 (d, J=7.2 Hz, 1H), 7.42 (d, J=8.8 Hz,3H), 7.49-7.51 (m, 1H), 8.18 (d, J=8.4 Hz, 1H), 8.32 (s, 1H).

Synthesis of(S)-2-[4-(4-naphthalen-2-ylethynyl-phenyl)-piperazine-1-sulfonylamino]-pentanoicacid (I-132)

¹H NMR (DMSO-d₆) δ: 0.88 (t, J=6.9 Hz, 3H), 1.30-1.70 (m, 4H), 3.05-3.40(m, 8H), 3.69 (m, 1H), 7.02 (d, J=9.0 Hz, 2H), 7.46 (d, J=8.7 Hz, 2H),7.52-7.60 (m, 3H), 7.86-8.00 (m, 4H), 8.12 (s, 1H), 12.77 (br s, 1H).

Synthesis of(R)-2-{4-[4-(4-cyano-6-methoxy-naphthalen-2-ylethynyl)-phenyl]1-piperazine-1-sulfonylamino}-propionicacid (I-133)

¹H NMR (DMSO-d₆) δ: 1.31 (d, J=7.2 Hz, 3H), 3.15-3.20 (m, 4H), 3.81 (t,J=6.0 Hz, 1H), 3.98 (s, 3H), 7.02 (d, J=8.4 Hz, 2H), 7.34 (s, 1H), 7.40(d, J=9.2 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.92 (d, J=9.2 Hz, 1H), 8.05(d, J=9.2 Hz, 1H), 8.20 (s, 1H), 8.41 (s, 1H).

According to the same manner as that described above, in the compoundsrepresented by the general formula (I′):

wherein R¹ is a group represented by:

Z is: (b1)-CH₂O—, (b2) —OCH₂—, (b3) —NHCH₂—, (b4) —CH₂NH—, (b5) —CH₂S—,(b6) —CH₂SO—, (b7) —CH₂SO₂—, (b8) —SCH₂—, (b9) —SOCH₂—, (b10) —SO₂CH₂—,(b11)-C(═O)C(═O)—, (b12) —CH₂CH₂—, (b 13) —CH═CH—, (b14) —C≡C—, or (b15)—NH—C(═O)—;A is a group represented by:

R³ is (d1) benzyl, (d2) indol-3-ylmethyl, (d3) isobutyl, (d4) methyl,(d5) 2-methylthioethyl, (d6) isopropyl, (d7) sec-butyl, (d8) t-butyl,(d9) n-propyl, (d10) n-butyl, (d11) hydroxymethyl, or (d12)4-hydroxybenzyl, (R¹, Z, A, R³)=(a1, b1, c1, d1), (a1, b1, c1, d2), (a1,b1, c1, d3), (a1, b1, c1, d4), (a1, b1, c1, d5), (a1, b1, c1, d6), (a1,b1, c1, d7), (a1, b1, c1, d8), (a1, b1, c1, d9), (a1, b1, c1, d10), (a1,b1, c1, d11), (a1, b1, c1, d12), (a1, b1, c2, d1), (a1, b1, c2, d2),(a1, b1, c2, d3), (a1, b1, c2, d4), (a1, b1, c2, d5), (a1, b1, c2, d6),(a1, b1, c2, d7), (a1, b1, c2, d8), (a1, b1, c2, d9), (a1, b1, c2, d10),(a1, b1, c2, d11), (a1, b1, c2, d12), (a1, b1, c3, d1), (a1, b1, c3,d2), (a1, b1, c3, d3), (a1, b1, c3, d4), (a1, b1, c3, d5), (a1, b1, c3,d6), (a1, b1, c3, d7), (a1, b1, c3, d8), (a1, b1, c3, d9), (a1, b1, c3,d10), (a1, b1, c3, d11), (a1, b1, c3, d12), (a1, b1, c4, d1), (a1, b1,c4, d2), (a1, b1, c4, d3), (a1, b1, c4, d4), (a1, b1, c4, d5), (a1, b1,c4, d6), (a1, b1, c4, d7), (a1, b1, c4, d8), (a1, b1, c4, d9), (a1, b1,c4, d10), (a1, b1, c4, d11), (a1, b1, c4, d12), (a1, b1, c5, d1), (a1,b1, c5, d2), (a1, b1, c5, d3), (a1, b1, c5, d4), (a1, b1, c5, d5), (a1,b1, c5, d6), (a1, b1, c5, d7), (a1, b1, c5, d8), (a1, b1, c5, d9), (a1,b1, c5, d10), (a1, b1, c5, d11), (a1, b1, c5, d12), (a1, b1, c6, d1),(a1, b1, c6, d2), (a1, b1, c6, d3), (a1, b1, c0, d4), (a1, b1, c6, d5),(a1, b1, c6, d6), (a1, b1, c6, d7), (a1, b1, c6, d8), (a1, b1, c6, d9),(a1, b1, c6, d10), (a1, b1, c6, d11), (a1, b1, c6, d12), (a1, b1, c7,d1), (a1, b1, c7, d2), (a1, b1, c7, d3), (a1, b1, c7, d4), (a1, b1, c7,d5), (a1, b1, c7, d6), (a1, b1, c7, d7), (a1, b1, c7, d8), (a1, b1, c7,d9), (a1, b1, c7, d10), (a1, b1, c7, d11), (a1, b1, c7, d12), (a1, b1,c8, d1), (a1, b1, c8, d2), (a1, b1, c8, d3), (a1, b1, c8, d4), (a1, b1,c8, d5), (a1, b1, c8, d6), (a1, b1, c8, d7), (a1, b1, c8, d8), (a1, b1,c8, d9), (a1, b1, c8, d10), (a1, b1, c8, d11), (a1, b1, c8, d12), (a1,b1, c9, d1), (a1, b1, c9, d2), (a1, b1, c9, d3), (a1, b1, c9, d4), (a1,b1, c9, d5), (a1, b1, c9, d6), (a1, b1, c9, d7), (a1, b1, c9, d8), (a1,b1, c9, d9), (a1, b1, c9, d10), (a1, b1, c9, d11), (a1, b1, c9, d12),(a1, b1, c10, d1), (a1, b1, c10, d2), (a1, b1, c10, d3), (a1, b1, c10,d4), (a1, b1, c10, d5), (a1, b1, c10, d6), (a1, b1, c0, d7), (a1, b1,c10, d8), (a1, b1, c10, d9), (a1, b1, c10, d10), (a1, b1, c10, d11),(a1, b1, c10, d12), (a1, b1, c11, d1), (a1, b1, c11, d2), (a1, b1, c11,d3), (a1, b1, c11, d4), (a1, b1, c11, d5), (a1, b1, c11, do), (a1, b1,c11, d7), (a1, b1, c11, d8), (a1, b1, c11, d9), (a1, b1, c11, d10), (a1,b1, c11, d11), (a1, b1, c11, d12), (a1, b1, c12, d1), (a1, b1, c12, d2),(a1, b1, c12, d3), (a1, b1, c12, d4), (a1, b1, c12, d5), (a1, b1, c12,d6), (a1, b1, c12, d7), (a1, b1, c12, d8), (a1, b1, c12, d9), (a1, b1,c12, d10), (a1, b1, c12, d11), (a1, b1, c12, d12), (a1, b1, c13, d1),(a1, b1, c13, d2), (a1, b1, c13, d3), (a1, b1, c13, d4), (a1, b1, c13,d5), (a1, b1, c13, d6), (a1, b1, c13, d7), (a1, b1, c13, d8), (a1, b1,c13, d9), (a1, b1, c13, d10), (a1, b1, c13, d11), (a1, b1, c13, d12),(a1, b2, c1, d1), (a1, b2, c1, d2), (a1, b2, c1, d3), (a1, b2, c1, d4),(a1, b2, c1, d5), (a1, b2, c1, d6), (a1, b2, c1, d7), (a1, b2, c1, d8),(a1, b2, c1, d9), (a1, b2, c1, d10), (a1, b2, c1, d11), (a1, b2, c1,d12), (a1, b2, c2, d1), (a1, b2, c2, d2), (a1, b2, c2, d3), (a1, b2, c2,d4), (a1, b2, c2, d5), (a1, b2, c2, d6), (a1, b2, c2, d7), (a1, b2, c2,d8), (a1, b2, c2, d9), (a1, b2, c2, d10), (a1, b2, c2, d11), (a1, b2,c2, d12), (a1, b2, c3, d1), (a1, b2, c3, d2), (a1, b2, c3, d3), (a1, b2,c3, d4), (a1, b2, c3, d5), (a1, b2, c3, d6), (a1, b2, c3, d7), (a1, b2,c3, d8), (a1, b2, c3, d9), (a1, b2, c3, d10), (a1, b2, c3, d11), (a1,b2, c3, d12), (a1, b2, c4, d1), (a1, b2, c4, d2), (a1, b2, c4, d3), (a1,b2, c4, d4), (a1, b2, c4, d5), (a1, b2, c4, d6), (a1, b2, c4, d7), (a1,b2, c4, d8), (a1, b2, c4, d9), (a1, b2, c4, d10), (a1, b2, c4, d11),(a1, b2, c4, d12), (a1, b2, c5, d1), (a1, b2, c5, d2), (a1, b2, c5, d3),(a1, b2, c5, d4), (a1, b2, c5, d5), (a1, b2, c5, d6), (a1, b2, c5, d7),(a1, b2, c5, d8), (a1, b2, c5, d9), (a1, b2, c5, d10), (a1, b2, c5,d11), (a1, b2, c5, d12), (a1, b2, c6, d1), (a1, b2, c6, d2), (a1, b2,c6, d3), (a1, b2, c6, d4), (a1, b2, c6, d5), (a1, b2, c6, d6), (a1, b2,c6, d7), (a1, b2, c6, d8), (a1, b2, c6, d9), (a1, b2, c6, d10), (a1, b2,c6, d11), (a1, b2, c6, d12), (a1, b2, c7, d1), (a1, b2, c7, d2), (a1,b2, c7, d3), (a1, b2, c7, d4), (a1, b2, c7, d5), (a1, b2, c7, d6), (a1,b2, c7, d7), (a1, b2, c7, d8), (a1, b2, c7, d9), (a1, b2, c7, d10), (a1,b2, c7, d11), (a1, b2, c7, d12), (a1, b2, c8, d1), (a1, b2, c8, d2),(a1, b2, c8, d3), (a1, b2, c8, d4), (a1, b2, c8, d5), (a1, b2, c8, d6),(a1, b2, c8, d7), (a1, b2, c8, d8), (a1, b2, c8, d9), (a1, b2, c8, d10),(a1, b2, c8, d11), (a1, b2, c8, d12), (a1, b2, c9, d1), (a1, b2, c9,d2), (a1, b2, c9, d3), (a1, b2, c9, d4), (a1, b2, c9, d5), (a1, b2, c9,d6), (a1, b2, c9, d7), (a1, b2, c9, d8), (a1, b2, c9, d9), (a1, b2, c9,d10), (a1, b2, c9, d11), (a1, b2, c9, d12), (a1, b2, c10, d1), (a1, b2,c10, d2), (a1, b2, c10, d3), (a1, b2, c10, d4), (a1, b2, c10, d5), (a1,b2, c10, d6), (a1, b2, c10, d7), (a1, b2, c10, d8), (a1, b2, c10, d9),(a1, b2, c10, d10), (a1, b2, c10, d11), (a1, b2, c10, d12), (a1, b2,c11, d1), (a1, b2, c11, d2), (a1, b2, c11, d3), (a1, b2, c11, d4), (a1,b2, c11, d5), (a1, b2, c11, d6), (a1, b2, c11, d7), (a1, b2, c11, d8),(a1, b2, c11, d9), (a1, b2, c11, d10), (a1, b2, c11, d11), (a1, b2, c11,d12), (a1, b2, c12, d1), (a1, b2, c12, d2), (a1, b2, c12, d3), (a1, b2,c12, d4), (a1, b2, c12, d5), (a1, b2, c12, d6), (a1, b2, c12, d7), (a1,b2, c12, d8), (a1, b2, c12, d9), (a1, b2, c12, d10), (a1, b2, c12, d11),(a1, b2, c12, d12), (a1, b2, c13, d1), (a1, b2, c13, d2), (a1, b2, c13,d3), (a1, b2, c13, d4), (a1, b2, c13, d5), (a1, b2, c13, d6), (a1, b2,c13, d7), (a1, b2, c13, d8), (a1, b2, c13, d9), (a1, b2, c13, d10), (a1,b2, c13, d11), (a1, b2, c13, d12), (a1, b3, c1, d1), (a1, b3, c1, d2),(a1, b3, c1, d3), (a1, b3, c1, d4), (a1, b3, c1, d5), (a1, b3, c1, d6),(a1, b3, c1, d7), (a1, b3, c1, d8), (a1, b3, c1, d9), (a1, b3, c1, d10),(a1, b3, c1, d11), (a1, b3, c1, d12), (a1, b3, c2, d1), (a1, b3, c2,d2), (a1, b3, c2, d3), (a1, b3, c2, d4), (a1, b3, c2, d5), (a1, b3, c2,d6), (a1, b3, c2, d7), (a1, b3, c2, d8), (a1, b3, c2, d9), (a1, b3, c2,d10), (a1, b3, c2, d11), (a1, b3, c2, d12), (a1, b3, c3, d1), (a1, b3,c3, d2), (a1, b3, c3, d3), (a1, b3, c3, d4), (a1, b3, c3, d5), (a1, b3,c3, d6), (a1, b3, c3, d7), (a1, b3, c3, d8), (a1, b3, c3, d9), (a1, b3,c3, d10), (a1, b3, c3, d11), (a1, b3, c3, d12), (a1, b3, c4, d1), (a1,b3, c4, d2), (a1, b3, c4, d3), (a1, b3, c4, d4), (a1, b3, c4, d5), (a1,b3, c4, d6), (a1, b3, c4, d7), (a1, b3, c4, d8), (a1, b3, c4, d9), (a1,b3, c4, d10), (a1, b3, c4, d11), (a1, b3, c4, d12), (a1, b3, c5, d1),(a1, b3, c5, d2), (a1, b3, c5, d3), (a1, b3, c5, d4), (a1, b3, c5, d5),(a1, b3, c5, d6), (a1, b3, c5, d7), (a1, b3, c5, d8), (a1, b3, c5, d9),(a1, b3, c5, d10), (a1, b3, c5, d11), (a1, b3, c5, d12), (a1, b3, c6,d1), (a1, b3, c6, d2), (a1, b3, c6, d3), (a1, b3, c6, d4), (a1, b3, c6,d5), (a1, b3, c6, d6), (a1, b3, c6, d7), (a1, b3, c6, d8), (a1, b3, c6,d9), (a1, b3, c6, d10), (a1, b3, c6, d11), (a1, b3, c6, d12), (a1, b3,c7, d1), (a1, b3, c7, d2), (a1, b3, c7, d3), (a1, b3, c7, d4), (a1, b3,c7, d5), (a1, b3, c7, d6), (a1, b3, c7, d7), (a1, b3, c7, d8), (a1, b3,c7, d9), (a1, b3, c7, d10), (a1, b3, c7, d11), (a1, b3, c7, d12), (a1,b3, c8, d1), (a1, b3, c8, d2), (a1, b3, c8, d3), (a1, b3, c8, d4), (a1,b3, c8, d5), (a1, b3, c8, d6), (a1, b3, c8, d7), (a1, b3, c8, d8), (a1,b3, c8, d9), (a1, b3, c8, d10), (a1, b3, c8, d11), (a1, b3, c8, d12),(a1, b3, c9, d1), (a1, b3, c9, d2), (a1, b3, c9, d3), (a1, b3, c9, d4),(a1, b3, c9, d5), (a1, b3, c9, d6), (a1, b3, c9, d7), (a1, b3, c9, d8),(a1, b3, c9, d9), (a1, b3, c9, d10), (a1, b3, c9, d11), (a1, b3, c9,d12), (a1, b3, c10, d1), (a1, b3, c10, d2), (a1, b3, c10, d3), (a1, b3,c10, d4), (a1, b3, c10, d5), (a1, b3, c10, d6), (a1, b3, c10, d7), (a1,b3, c10, d8), (a1, b3, c10, d9), (a1, b3, c10, d10), (a1, b3, c10, d11),(a1, b3, c10, d12), (a1, b3, c11, d1), (a1, b3, c11, d2), (a1, b3, c11,d3), (a1, b3, c11, d4), (a1, b3, c11, d5), (a1, b3, c11, d6), (a1, b3,c11, d7), (a1, b3, c11, d8), (a1, b3, c11, d9), (a1, b3, c11, d10), (a1,b3, c11, d11), (a1, b3, c11, d12), (a1, b3, c12, d1), (a1, b3, c12, d2),(a1, b3, c12, d3), (a1, b3, c12, d4), (a1, b3, c12, d5), (a1, b3, c12,d6), (a1, b3, c12, d7), (a1, b3, c12, d8), (a1, b3, c12, d9), (a1, b3,c12, d10), (a1, b3, c12, d11), (a1, b3, c12, d12), (a1, b3, c13, d1),(a1, b3, c13, d2), (a1, b3, c13, d3), (a1, b3, c13, d4), (a1, b3, c13,d5), (a1, b3, c13, d6), (a1, b3, c13, d7), (a1, b3, c13, d8), (a1, b3,c13, d9), (a1, b3, c13, d10), (a1, b3, c13, d11), (a1, b3, c13, d12),(a1, b4, c1, d1), (a1, b4, c1, d2), (a1, b4, c1, d3), (a1, b4, c1, d4),(a1, b4, c1, d5), (a1, b4, c1, d6), (a1, b4, c1, d7), (a1, b4, c1, d8),(a1, b4, c1, d9), (a1, b4, c1, d10), (a1, b4, c1, d11), (a1, b4, c1,d12), (a1, b4, c2, d1), (a1, b4, c2, d2), (a1, b4, c2, d3), (a1, b4, c2,d4), (a1, b4, c2, d5), (a1, b4, c2, d6), (a1, b4, c2, d7), (a1, b4, c2,d8), (a1, b4, c2, d9), (a1, b4, c2, d10), (a1, b4, c2, d11), (a1, b4,c2, d12), (a1, b4, c3, d1), (a1, b4, c3, d2), (a1, b4, c3, d3), (a1, b4,c3, d4), (a1, b4, c3, d5), (a1, b4, c3, d6), (a1, b4, c3, d7), (a1, b4,c3, d8), (a1, b4, c3, d9), (a1, b4, c3, d10), (a1, b4, c3, d11), (a1,b4, c3, d12), (a1, b4, c4, d1), (a1, b4, c4, d2), (a1, b4, c4, d3), (a1,b4, c4, d4), (a1, b4, c4, d5), (a1, b4, c4, d6), (a1, b4, c4, d7), (a1,b4, c4, d8), (a1, b4, c4, d9), (a1, b4, c4, d10), (a1, b4, c4, d11),(a1, b4, c4, d12), (a1, b4, c5, d1), (a1, b4, c5, d2), (a1, b4, c5, d3),(a1, b4, c5, d4), (a1, b4, c5, d5), (a1, b4, c5, d6), (a1, b4, c5, d7),(a1, b4, c5, d8), (a1, b4, c5, d9), (a1, b4, c5, d10), (a1, b4, c5,d11), (a1, b4, c5, d12), (a1, b4, c6, d1), (a1, b4, c6, d2), (a1, b4,c6, d3), (a1, b4, c6, d4), (a1, b4, c6, d5), (a1, b4, c6, d6), (a1, b4,c6, d7), (a1, b4, c6, d8), (a1, b4, c6, d9), (a1, b4, c6, d10), (a1, b4,c6, d11), (a1, b4, c6, d12), (a1, b4, c7, d1), (a1, b4, c7, d2), (a1,b4, c7, d3), (a1, b4, c7, d4), (a1, b4, c7, d5), (a1, b4, c7, d6), (a1,b4, c7, d7), (a1, b4, c7, d8), (a1, b4, c7, d9), (a1, b4, c7, d10), (a1,b4, c7, d11), (a1, b4, c7, d12), (a1, b4, c8, d1), (a1, b4, c8, d2),(a1, b4, c8, d3), (a1, b4, c8, d4), (a1, b4, c8, d5), (a1, b4, c8, d6),(a1, b4, c8, d7), (a1, b4, c8, d8), (a1, b4, c8, d9), (a1, b4, c8, d10),(a1, b4, c8, d11), (a1, b4, c8, d12), (a1, b4, c9, d1), (a1, b4, c9,d2), (a1, b4, c9, d3), (a1, b4, c9, d4), (a1, b4, c9, d5), (a1, b4, c9,d6), (a1, b4, c9, d7), (a1, b4, c9, d8), (a1, b4, c9, d9), (a1, b4, c9,d10), (a1, b4, c9, d11), (a1, b4, c9, d12), (a1, b4, c10, d1), (a1, b4,c10, d2), (a1, b4, c10, d3), (a1, b4, c10, d4), (a1, b4, c10, d5), (a1,b4, c10, d6), (a1, b4, c10, d7), (a1, b4, c10, d8), (a1, b4, c10, d9),(a1, b4, c10, d10), (a1, b4, c10, d11), (a1, b4, c10, d12), (a1, b4,c11, d1), (a1, b4, 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d2),(a2, b4, c12, d3), (a2, b4, c12, d4), (a2, b4, c12, d5), (a2, b4, c12,d6), (a2, b4, c12, d7), (a2, b4, c12, d8), (a2, b4, c12, d9), (a2, b4,c12, d10), (a2, b4, c12, d11), (a2, b4, c12, d12), (a2, b4, c13, d1),(a2, b4, c13, d2), (a2, b4, c13, d3), (a2, b4, c13, d4), (a2, b4, c13,d5), (a2, b4, c13, d6), (a2, b4, c13, d7), (a2, b4, c13, d8), (a2, b4,c13, d9), (a2, b4, c13, d10), (a2, b4, c13, d11), (a2, b4, c13, d12),(a2, b5, c1, d1), (a2, b5, c1, d2), (a2, b5, c1, d3), (a2, b5, c1, d4),(a2, b5, c1, d5), (a2, b5, c1, d6), (a2, b5, c1, d7), (a2, b5, c1, d8),(a2, b5, c1, d9), (a2, b5, c1, d10), (a2, b5, c1, d11), (a2, b5, c1,d12), (a2, b5, c2, d1), (a2, b5, c2, d2), (a2, b5, c2, d3), (a2, b5, c2,d4), (a2, b5, c2, d5), (a2, b5, c2, d6), (a2, b5, c2, d7), (a2, b5, c2,d8), (a2, b5, c2, d9), (a2, b5, c2, d10), (a2, b5, c2, d11), (a2, b5,c2, d12), (a2, b5, c3, d1), (a2, b5, c3, d2), (a2, b5, c3, d3), (a2, b5,c3, d4), (a2, b5, c3, d5), (a2, b5, c3, d6), (a2, b5, c3, d7), (a2, b5,c3, d8), (a2, 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d4), (a2, b5, c8, d5), (a2, b5, c8, d6),(a2, b5, c8, d7), (a2, b5, c8, d8), (a2, b5, c8, d9), (a2, b5, c8, d10),(a2, b5, c8, d11), (a2, b5, c8, d12), (a2, b5, c9, d1), (a2, b5, c9,d2), (a2, b5, c9, d3), (a2, b5, c9, d4), (a2, b5, c9, d5), (a2, b5, c9,d6), (a2, b5, c9, d7), (a2, b5, c9, d8), (a2, b5, c9, d9), (a2, b5, c9,d10), (a2, b5, c9, d11), (a2, b5, c9, d12), (a2, b5, c10, d1), (a2, b5,c10, d2), (a2, b5, c10, d3), (a2, b5, c10, d4), (a2, b5, c10, d5), (a2,b5, c10, d6), (a2, b5, c10, d7), (a2, b5, c10, d8), (a2, b5, c10, d9),(a2, b5, c10, d10), (a2, b5, c10, d11), (a2, b5, c10, d12), (a2, b5,c11, d1), (a2, b5, c11, d2), (a2, b5, c11, d3)₇ (a2, b5, c11, d4), (a2,b5, c11, d5), (a2, b5, c11, d6), (a2, b5, c11, d7), (a2, b5, c11, d8),(a2, b5, c11, d9), (a2, b5, c11, d10), (a2, b5, c11, d11), (a2, b5, c11,d12), (a2, b5, c12, d1), (a2, b5, c12, d2), (a2, b5, c12, d3), (a2, b5,c12, d4), (a2, b5, c12, d5), (a2, b5, c12, d6), (a2, b5, c12, d7), (a2,b5, c12, d8), (a2, b5, c12, d9), (a2, b5, c12, d10), (a2, b5, c12, d11),(a2, b5, c12, d12), (a2, b5, c13, d1), (a2, b5, c13, d2), (a2, b5, c13,d3), (a2, b5, c13, d4), (a2, b5, c13, d5), (a2, b5, c13, d6), (a2, b5,c13, d7), (a2, b5, c13, d8), (a2, b5, c13, d9), (a2, b5, c13, d10), (a2,b5, c13, d11), (a2, b5, c13, d12), (a2, b6, c1, d11), (a2, b6, c1, d2),(a2, b6, c1, d3), (a2, b6, c1, d4), (a2, b6, c1, d5), (a2, b6, c1, d6),(a2, b6, c1, d7), (a2, b6, c1, d8), (a2, b6, c1, d9), (a2, b6, c1, d10),(a2, b6, c1, d11), (a2, b6, c1, d12), (a2, b6, c2, d1), (a2, b6, c2,d2), (a2, b6, c2, d3), (a2, b6, c2, d4), (a2, b6, c2, d5), (a2, b6, c2,d6), (a2, b6, c2, d7), (a2, b6, c2, d8), (a2, b6, c2, d9), (a2, b6, c2,d10), (a2, b6, c2, d11), (a2, b6, c2, d12), (a2, b6, c3, d1), (a2, b6,c3, d2), (a2, b6, c3, d3), (a2, b6, c3, d4), (a2, b6, c3, d5), (a2, b6,c3, d6), (a2, b6, c3, d7), (a2, b6, c3, d8), (a2, b6, c3, d9), (a2, b6,c3, d10), (a2, b6, c3, d11), (a2, b6, c3, d12), (a2, b6, c4, d1), (a2,b6, c4, d2), (a2, b6, c4, d3), (a2, b6, c4, d4), (a2, b6, c4, d5), (a2,b6, c4, d6), (a2, b6, c4, d7), (a2, b6, c4, d8), (a2, b6, c4, d9), (a2,b6, c4, d10), (a2, b6, c4, d11), (a2, b6, c4, d12), (a2, b6, c5, d1),(a2, b6, c5, d2), (a2, b6, c5, d3), (a2, b6, c5, d4), (a2, b6, c5, d5),(a2, b6, c5, d6), (a2, b6, c5, d7), (a2, b6, c5, d8), (a2, b6, c5, d9),(a2, b6, c5, d10), (a2, b6, c5, d11), (a2, b6, c5, d12), (a2, b6, c6,d1), (a2, b6, c6, d2), (a2, b6, c6, d3), (a2, b6, c6, d4), (a2, b6, c6,d5), (a2, b6, c6, d6), (a2, b6, c6, d7), (a2, b6, c6, d8), (a2, b6, c6,d9), (a2, b6, c6, d10), (a2, b6, c6, d11), (a2, b6, c6, d12), (a2, b6,c7, d1), (a2, b6, c7, d2), (a2, b6, c7, d3), (a2, b6, c7, d4), (a2, b6,c7, d5), (a2, b6, c7, d6), (a2, b6, c7, d7), (a2, b6, c7, d8), (a2, b6,c7, d9), (a2, b6, c7, d10), (a2, b6, c7, d11), (a2, b6, c7, d12), (a2,b6, c8, d1), (a2, b6, c8, d2), (a2, b6, c8, d3), (a2, b6, c8, d4), (a2,b6, c8, d5), (a2, b6, c8, d6), (a2, b6, c8, d7), (a2, b6, c8, d8), (a2,b6, c8, d9), (a2, b6, c8, d10), (a2, b6, c8, d11), (a2, b6, c8, d12),(a2, b6, c9, d1), (a2, b6, c9, d2), (a2, b6, c9, d3), (a2, b6, c9, d4),(a2, b6, c9, d5), (a2, b6, c9, d6), (a2, b6, c9, d7), (a2, b6, c9, d8),(a2, b6, c9, d9), (a2, b6, c9, d10), (a2, b6, c9, d11), (a2, b6, c9,d12), (a2, b6, c10, d1), (a2, b6, c10, d2), (a2, b6, c10, d3), (a2, b6,c10, d4), (a2, b6, c10, d5), (a2, b6, c10, d6), (a2, b6, c10, d7), (a2,b6, c10, d8), (a2, b6, c10, d9), (a2, b6, c10, d10), (a2, b6, c10, d11),(a2, b6, c10, d12), (a2, b6, c11, d1), (a2, b6, c1, d2), (a2, b6, c11,d3), (a2, b6, c11, d4), (a2, b6, c11, d5), (a2, b6, c11, d6), (a2, b6,c11, d7), (a2, b6, c11, d8), (a2, b6, c11, d9), (a2, b6, c11, d10), (a2,b6, c11, d11), (a2, b6, c11, d12), (a2, b6, c12, d1), (a2, b6, c12, d2),(a2, b6, c12, d3), (a2, b6, c12, d4), (a2, b6, c12, d5), (a2, b6, c12,d6), (a2, b6, c12, d7), (a2, b6, c12, d8), (a2, b6, c12, d9), (a2, b6,c12, d10), (a2, b6, c12, d11), (a2, b6, c12, d12), (a2, b6, c13, d1),(a2, b6, c13, d2), (a2, b6, c13, d3), (a2, b6, c13, d4), (a2, b6, c13,d5), (a2, b6, c13, d6), (a2, b6, c13, d7), (a2, b6, c13, d8), (a2, b6,c13, d9), (a2, b6, c13, d10), (a2, b6, c13, d11), (a2, b6, c13, d12),(a2, b7, c1, d1), (a2, b7, c1, d2), (a2, b7, c1, d3), (a2, b7, c1, d4),(a2, b7, c1, d5), (a2, b7, c1, d6), (a2, b7, c1, d7), (a2, b7, c1, d8),(a2, b7, c1, d9), (a2, b7, c1, d10), (a2, b7, c1, d11), (a2, b7, c1,d12), (a2, b7, c2, d1), (a2, b7, c2, d2), (a2, b7, c2, d3), (a2, b7, c2,d4), (a2, b7, c2, d5), (a2, b7, c2, d6), (a2, b7, c2, d7), (a2, b7, c2,d8), (a2, b7, c2, d9), (a2, b7, c2, d10), (a2, b7, c2, d11), (a2, b7,c2, d12), (a2, b7, c3, d1), (a2, b7, c3, d2), (a2, b7, c3, d3), (a2, b7,c3, d4), (a2, b7, c3, d5), (a2, b7, c3, d6), (a2, b7, c3, d7), (a2, b7,c3, d8), (a2, b7, c3, d9), (a2, b7, c3, d10), (a2, b7, c3, d11), (a2,b7, c3, d12), (a2, b7, c4, d1), (a2, b7, c4, d2), (a2, b7, c4, d3), (a2,b7, c4, d4), (a2, b7, c4, d5), (a2, b7, c4, d6), (a2, b7, c4, d7), (a2,b7, c4, d8), (a2, b7, c4, d9), (a2, b7, c4, d10), (a2, b7, c4, d11),(a2, b7, c4, d12), (a2, b7, c5, d1), (a2, b7, c5, d2), (a2, b7, c5, d3),(a2, b7, c5, d4), (a2, b7, c5, d5), (a2, b7, c5, d6), (a2, b7, c5, d7),(a2, b7, c5, d8), (a2, b7, c5, d9), (a2, b7, c5, d10), (a2, b7, c5,d11), (a2, b7, c5, d12), (a2, b7, c6, d1), (a2, b7, c6, d2), (a2, b7,c6, d3), (a2, b7, c6, d4), (a2, b7, c6, d5), (a2, b7, c6, d6), (a2, b7,c6, d7), (a2, b7, c6, d8), (a2, b7, c6, d9), (a2, b7, c6, d10), (a2, b7,c6, d11), (a2, b7, c6, d12), (a2, b7, c7, d1), (a2, b7, c7, d2), (a2,b7, c7, d3), (a2, b7, c7, d4), (a2, b7, c7, d5), (a2, b7, c7, d6), (a2,b7, c7, d7), (a2, b7, c7, d8), (a2, b7, c7, d9), (a2, b7, c7, d10), (a2,b7, c7, d11), (a2, b7, c7, d12), (a2, b7, c8, d1), (a2, b7, c8, d2),(a2, b7, c8, d3), (a2, b7, c8, d4), (a2, b7, c8, d5), (a2, b7, c8, d6),(a2, b7, c8, d7), (a2, b7, c8, d8), (a2, b7, c8, d9), (a2, b7, c8, d10),(a2, b7, c8, d11), (a2, b7, c8, d12), (a2, b7, c9, d1), (a2, b7, c9,d2), (a2, b7, c9, d3), (a2, b7, c9, d4), (a2, b7, c9, d5), (a2, b7, c97d6), (a2, b7, c9, d7), (a2, b7, c9, d8), (a2, b7, c9, d9), (a2, b7, c9,d10), (a2, b7, c9, d11), (a2, b7, c9, d12), (a2, b7, c10, d1), (a2, b7,c10, d2), (a2, b7, c10, d3), (a2, b7, c0, d4), (a2, b7, c10, d5), (a2,b7, c10, d6), (a2, b7, c10, d7), (a2, b7, c10, d8), (a2, b7, c10, d),(a2, b7, c10, d10), (a2, b7, c10, d11), (a2, b7, c10, d12), (a2, b7,c11, d1), (a2, b7, c11, d2), (a2, b7, c11, d3), (a2, b7, c11, d4), (a2,b7, c11, d5), (a2, b7, c11, d6), (a2, b7, c11, d7), (a2, b7, c11, d8),(a2, b7, c11, d9), (a2, b7, c11, d10), (a2, b7, c11, d11), (a2, b7, c11,d12), (a2, b7, c12, d1), (a2, b7, c12, d2), (a2, b7, c12, d3), (a2, b7,c12, d4), (a2, b7, c12, d5), (a2, b7, c12, d6), (a2, b7, c12, d7), (a2,b7, c12, d8), (a2, b7, c12, d9), (a2, b7, c12, d10), (a2, b7, c12, d11),(a2, b7, c12, d12), (a2, b7, c13, d1), (a2, b7, c13, d2), (a2, b7, c13,d3), (a2, b7, c13, d4), (a2, b7, c13, d5), (a2, b7, c13, d6), (a2, b7,c13, d7), (a2, b7, c13, d8), (a2, b7, c13, d9), (a2, b7, c13, d10), (a2,b7, c13, d11), (a2, b7, c13, d12), (a2, b8, c1, d1), (a2, b8, c1, d2),(a2, b8, c1, d3), (a2, b8, c1, d4), (a2, b8, c1, d5), (a2, b8, c1, d6),(a2, b8, c1, d7), (a2, b8, c1, d8), (a2, b8, c1, d9), (a2, b8, c1, d10),(a2, b5, c1, d11), (a2, b8, c1, d12), (a2, b5, c2, d1), (a2, b5, c2,d2), (a2, b8, c2, d3), (a2, b8, c2, d4), (a2, b8, c2, d5), (a2, b8, c2,d6), (a2, b8, c2, d7), (a2, b8, c2, d8), (a2, b8, c2, d9), (a2, b8, c2,d10), (a2, b8, c2, d11), (a2, b8, c2, d12), (a2, b8, c3, d1), (a2, b8,c3, d2), (a2, b8, c3, d3), (a2, b8, c3, d4), (a2, b8, c3, d5), (a2, b8,c3, d6), (a2, b8, c3, d7), (a2, b8, c3, d8), (a2, b8, c3, d9), (a2, b8,c3, d10), (a2, b8, c3, d11), (a2, b8, c3, d12), (a2, b8, c4, d1), (a2,b8, c4, d2), (a2, b8, c4, d3), (a2, b8, c4, d4), (a2, b8, c4, d5), (a2,b8, c4, d6), (a2, b8, c4, d7), (a2, b8, c4, d8), (a2, b8, c4, d9), (a2,b8, c4, d10), (a2, b8, c4, d11), (a2, b8, c4, d12), (a2, b8, c5, d1),(a2, b8, c5, d2), (a2, b8, c5, d3), (a2, b8, c5, d4), (a2, b8, c5, d5),(a2, b8, c5, d6), (a2, b8, c5, d7), (a2, b8, c5, d8), (a2, b8, c5, d9),(a2, b8, c5, d10), (a2, b8, c5, d11), (a2, b8, c5, d12), (a2, b8, c6,d1), (a2, b8, c6, d2), (a2, b8, c6, d3), (a2, b8, c6, d4), (a2, b8, c6,d5), (a2, b8, c6, d6), (a2, b8, c6, d7), (a2, b8, c6, d8), (a2, b8, c6,d9), (a2, b8, c6, d10), (a2, b8, c6, d11), (a2, b8, c6, d12), (a2, b8,c7, d1), (a2, b8, c7, d2), (a2, b8, c7, d3), (a2, b8, c7, d4), (a2, b8,c7, d5), (a2, b8, c7, d6), (a2, b8, c7, d7), (a2, b8, c7, d8), (a2, b8,c7, d9), (a2, b8, c7, d10), (a2, b8, c7, d11), (a2, b8, c7, d12), (a2,b8, c8, d1), (a2, b8, c8, d2), (a2, b8, c8, d3), (a2, b8, c8, d4), (a2,b8, c8, d5), (a2, b8, c8, d6), (a2, b8, c8, d7), (a2, b8, c8, d8), (a2,b8, c8, d9), (a2, b8, c8, d10)₇ (a2, b8, c8, d11), (a2, b8, c8, d12),(a2, b8, c9, d1), (a2, b8, c9, d2), (a2, b8, c9, d3), (a2, b8, c9, d4),(a2, b8, c9, d5), (a2, b8, c9, d6), (a2, b8, c9, d7), (a2, b8, c9, d8),(a2, b8, c9, d9), (a2, b8, c9, d10), (a2, b8, c9, d11), (a2, b8, c9,d12), (a2, b8, c10, d1), (a2, b8, c10, d2), (a2, b8, c10, d3), (a2, b8,c0, d4), (a2, b8, c10, d5), (a2, b8, c10, d6), (a2, b8, c10, d7), (a2,b8, c10, d8), (a2, b8, c10, d9), (a2, b8, c10, d10), (a2, b8, c10, d11),(a2, b8, c10, d12), (a2, b8, c11, d1), (a2, b8, c11, d2), (a2, b8, c11,d3), (a2, b8, c11, d4), (a2, b8, c11, d5), (a2, b8, c11, d6), (a2, b8,c11, d7), (a2, b8, c11, d8), (a2, b8, c11, d9), (a2, b8, c11, d10), (a2,b8, c11, d11), (a2, b8, c11, d12), (a2, b8, c12, d1), (a2, b8, c12, d2),(a2, b8, c12, d3), (a2, b8, c12, d4), (a2, b8, c12, d5), (a2, b8, c12,d6), (a2, b8, c12, d7), (a2, b8, c12, d8), (a2, b8, c12, d9), (a2, b8,c12, d10), (a2, b8, c12, d11), (a2, b8, c12, d12), (a2, b8, c13, d1),(a2, b8, c13, d2), (a2, b8, c13, d3), (a2, b8, c13, d4), (a2, b8, c13,d5), (a2, b8, c13, d6), (a2, b8, c13, d7), (a2, b8, c13, d8), (a2, b8,c13, d9), (a2, b8, c13, d10), (a2, b8, c13, d11), (a2, b8, c13, d12),(a2, b9, c1, d1), (a2, b9, c1, d2), (a2, b9, c1, d3), (a2, b9, c1, d4),(a2, b9, c1, d5), (a2, b9, c1, d6), (a2, b9, c1, d7), (a2, b9, c1, d8),(a2, b9, c1, d9), (a2, b9, c1, d10), (a2, b9, c1, d11), (a2, b9, c1,d12), (a2, b9, c2, d1), (a2, b9, c2, d2), (a2, b9, c2, d3), (a2, b9, c2,d4), (a2, b9, c2, d5), (a2, b9, c2, d6), (a2, b9, c2, d7), (a2, b9, c2,d8), (a2, b9, c2, d9), (a2, b9, c2, d10), (a2, b9, c2, d11), (a2, b9,c2, d12), (a2, b9, c3, d1), (a2, b9, c3, d2), (a2, b9, c3, d3), (a2, b9,c3, d4), (a2, b9, c3, d5), (a2, b9, c3, d6), (a2, b9, c3, d7), (a2, b9,c3, d8), (a2, b9, c3, d9), (a2, b9, c3, d10), (a2, b9, c3, d11), (a2,b9, c3, d12), (a2, b9, c4, d1), (a2, b9, c4, d2), (a2, b9, c4, d3), (a2,b9, c4, d4), (a2, b9, c4, d5), (a2, b9, c4, d6), (a2, b9, c4, d7), (a2,b9, c4, d8), (a2, b9, c4, d9), (a2, b9, c4, d10), (a2, b9, c4, d11),(a2, b9, c4, d12), (a2, b9, c5, d1), (a2, b9, c5, d2), (a2, b9, c5, d3),(a2, b9, c5, d4), (a2, b9, c5, d5), (a2, b9, c5, d6), (a2, b9, c5, d7),(a2, b9, c5, d8), (a2, b9, c5, d9), (a2, b9, c5, d10), (a2, b9, c5,d11), (a2, b9, c5, d12), (a2, b9, c6, d1), (a2, b9, c6, d2), (a2, b9,c6, d3), (a2, b9, c6, d4), (a2, b9, c6, d5), (a2, b9, c6, d6), (a2, b9,c6, d7), (a2, b9, c6, d8), (a2, b9, c6, d9), (a2, b9, c6, d10), (a2, b9,c6, d11), (a2, b9, c6, d12), (a2, b9, c7, d1), (a2, b9, c7, d2), (a2,b9, c7, d3), (a2, b9, c7, d4), (a2, b9, c7, d5), (a2, b9, c7, d6), (a2,b9, c7, d7), (a2, b9, c7, d8), (a2, b9, c7, d9), (a2, b9, c7, d10), (a2,b9, c7, d11), (a2, b9, c7, d12), (a2, b9, c8, d1), (a2, b9, c8, d2),(a2, b9, c8, d3), (a2, b9, c8, d4), (a2, b9, c8, d5), (a2, b9, c8, d6),(a2, b9, c8, d7), (a2, b9, c8, d8), (a2, b9, c8, d9), (a2, b9, c8, d10),(a2, b9, c8, d11), (a2, b9, c8, d12), (a2, b9, c9, d1), (a2, b9, c9,d2), (a2, b9, c9, d3), (a2, b9, c9, d4), (a2, b9, c9, d5), (a2, b9, c9,d6), (a2, b9, c9, d7), (a2, b9, c9, d8), (a2, b9, c9, d9), (a2, b9, c9,d10), (a2, b9, c9, d11), (a2, b9, c9, d12), (a2, b9, c10, d1), (a2, b9,c10, d2), (a2, b9, c10, d3), (a2, b, c10, d4), (a2, b9, c10, d5), (a2,b9, c10, d6), (a2, b9, c10, d7), (a2, b9, c10, d8), (a2, b9, c10, d9),(a2, b9, c10, d10), (a2, b9, c10, d11), (a2, b9, c10, d12), (a2, b9,c11, d1), (a2, b9, c11, d2), (a2, b9, c11, d3), (a2, b9, c11, d4), (a2,b9, c11, d5), (a2, b9, c11, d6), (a2, b9, c11, d7), (a2, b9, c11, d8),(a2, b9, c11, d9), (a2, b9, c11, d10), (a2, b9, c11, d11), (a2, b9, c11,d12), (a2, b9, c12, d1), (a2, b9, c12, d2), (a2, b9, c12, d3), (a2, b9,c12, d4) (a2, b9, c12, d5), (a2, b9, c12, d6), (a2, b9, c12, d7), (a2,b9, c12, d8), (a2, b9, c12, d9), (a2, b9, c12, d10), (a2, b9, c12, d11),(a2, b9, c12, d12), (a2, b9, c13, d1), (a2, b9, c13, d2), (a2, b9, c13,d3), (a2, b9, c13, d4), (a2, b9, c13, d5), (a2, b9, c13, d6), (a2, b9,c13, d7), (a2, b9, c13, d8), (a2, b9, c13, d9), (a2, b9, c13, d10), (a2,b9, c13, d11), (a2, b9, c13, d12), (a2, b10, c1, d1), (a2, b10, c1, d2),(a2, b10, c1, d3), (a2, b10, c1, d4), (a2, b10, c1, d5), (a2, b10, c1,d6), (a2, b10, c1, d7), (a2, b10, c1, d8), (a2, b10, c1, d9), (a2, b10,c1, d10), (a2, b10, c1, d11), (a2, b10, c1, d12), (a2, b10, c2, d1),(a2, b10, c2, d2), (a2, b10, c2, d3), (a2, b10, c2, d4), (a2, b10, c2,d5), (a2, b10, c2, d6), (a2, b10, c2, d7), (a2, b10, c2, d8), (a2, b10,c2, d9), (a2, b10, c2, d10), (a2, b10, c2, d11), (a2, b10, c2, d12),(a2, b10, c3, d1), (a2, b10, c3, d2), (a2, b10, c3, d3), (a2, b10, c3,d4), (a2, b10, c3, d5), (a2, b10, c3, d6), (a2, b10, c3, d7), (a2, b10,c3, d8), (a2, b10, c3, d9), (a2, b10, c3, d10), (a2, b10, c3, d11), (a2,b10, c3, d12), (a2, b10, c4, d1), (a2, b10, c4, d2), (a2, b10, c4, d3),(a2, b10, c4, d4), (a2, b10, c4, d5), (a2, b10, c4, d6), (a2, b10, c4,d7), (a2, b10, c4, d8), (a2, b10, c4, d9), (a2, b10, c4, d10), (a2, b10,c4, d11), (a2, b10, c4, d12), (a2, b10, c5, d1), (a2, b10, c5, d2), (a2,b10, c5, d3), (a2, b10, c5, d4), (a2, b10, c5, d5), (a2, b10, c5, d6),(a2, b10, c5, d7), (a2, b10, c5, d8), (a2, b10, c5, d9), (a2, b10, c5,d10), (a2, b10, c5, d11), (a2, b10, c5, d12), (a2, b10, c6, d1), (a2,b10, c6, d2), (a2, b10, c6, d3), (a2, b10, c6, d4), (a2, b10, c6, d5),(a2, b10, c6, d6), (a2, b10, c6, d7), (a2, b10, c6, d8), (a2, b10, c6,d9), (a2, b10, c6, d10), (a2, b10, c6, d11), (a2, b10, c6, d12), (a2,b10, c7, d1), (a2, b10, c7, d2), (a2, b10, c7, d3), (a2, b10, c7, d4),(a2, b10, c7, d5), (a2, b10, c7, d6), (a2, b10, c7, d7), (a2, b10, c7,d8), (a2, b10, c7, d9), (a2, b10, c7, d10), (a2, b10, c7, d11), (a2,b10, c7, d12), (a2, b10, c8, d1), (a2, b10, c8, d2), (a2, b10, c8, d3),(a2, b10, c8, d4), (a2, b10, c8, d5), (a2, b10, c8, d6), (a2, b10, c8,d7), (a2, b10, c8, d8), (a2, b10, c8, d9), (a2, b10, c8, d10), (a2, b10,c8, d11), (a2, b10, c8, d12), (a2, b10, c9, d1), (a2, b10, c9, d2), (a2,b10, c9, d3), (a2, b10, c9, d4), (a2, b10, c9, d5), (a2, b10, c9, d6),(a2, b10, c9, d7), (a2, b10, c9, d8), (a2, b10, c9, d9), (a2, b10, c9,d10), (a2, b10, c9, d11), (a2, b10, c9, d12), (a2, b10, c10, d1), (a2,b10, c10, d2), (a2, b10, c10, d3), (a2, b10, c10, d4), (a2, b10, c10,d5), (a2, b10, c10, d6), (a2, b10, c10, d7), (a2, b10, c10, d8), (a2,b10, c10, d9), (a2, b10, c10, d10), (a2, b10, c10, d11), (a2, b10, c10,d12), (a2, b10, c11, d1), (a2, b10, c11, d2), (a2, b10, c11, d3), (a2,b10, c11, d4), (a2, b10, c11, d5), (a2, b10, c11, d6), (a2, b10, c11,d7), (a2, b10, c11, d8), (a2, b10, c11, d9), (a2, b10, c11, d10), (a2,b10, c11, d11), (a2, b10, c11, d12), (a2, b10, c12, d1), (a2, b10, c12,d2), (a2, b10, c12, d3), (a2, b10, c12, d4), (a2, b10, c12, d5), (a2,b10, c12, d6), (a2, b10, c12, d7), (a2, b10, c12, d8), (a2, b10, c12,d9), (a2, b10, c12, d10), (a2, b10, c12, d11), (a2, b10, c12, d12), (a2,b10, c13, d1), (a2, b10, c13, d2), (a2, b10, c13, d3), (a2, b10, c13,d4), (a2, b10, c13, d5), (a2, b10, c13, d6), (a2, b10, c13, d7), (a2,b10, c13, d8), (a2, b10, c13, d9), (a2, b10, c13, d10), (a2, b10, c13,d11), (a2, b10, c13, d12), (a2, b11, c1, d1), (a2, b11, c1, d2), (a2,b11, c1, d3), (a2, b11, c1, d4), (a2, b11, c1, d5), (a2, b11, c1, d6),(a2, b11, c1, d7), (a2, b11, c1, d8), (a2, b11, c1, d9), (a2, b11, c1,d10), (a2, b11, c1, d11), (a2, b11, c1, d12), (a2, b11, c2, d1), (a2,b11, c2, d2), (a2, b11, c2, d3), (a2, b11, c2, d4), (a2, b11, c2, d5),(a2, b11, c2, d6), (a2, b11, c2, d7), (a2, b11, c2, d8), (a2, b11, c2,d9), (a2, b11, c2, d10), (a2, b11, c2, d11), (a2, b11, c2, d12), (a2,b11, c3, d1), (a2, b11, c3, d2), (a2, b11, c3, d3), (a2, b11, c3, d4),(a2, b11, c3, d5), (a2, b11, c3, d6), (a2, b11, c3, d7), (a2, b11, c3,d8), (a2, b11, c3, d9), (a2, b11, c3, d10), (a2, b11, c3, d11), (a2,b11, c3, d12), (a2, b11, c4, d1), (a2, b11, c4, d2), (a2, b11, c4, d3),(a2, b11, c4, d4), (a2, b11, c4, dc), (a2, b11, c4, d6), (a2, b11, c4,d7), (a2, b11, c4, d8), (a2, b11, c4, d9), (a2, b11, c4, d10), (a2, b11,c4, d11), (a2, b11, c4, d12), (a2, b11, c5, d1), (a2, b11, c5, d2), (a2,b11, c5, d3), (a2, b11, c5, d4), (a2, b11, c5, d5), (a2, b11, c5, d6),(a2, b11, c5, d7), (a2, b11, c5, d8), (a2, b11, c5, d9), (a2, b11, c5,d10), (a2, b11, c5, d11), (a2, b11, c5, d12), (a2, b11, c6, d1), (a2,b11, c6, d2), (a2, b11, c6, d3), (a2, b11, c6, d4), (a2, b11, c6, d5),(a2, b11, c6, d6), (a2, b11, c6, d7), (a2, b11, c6, d8), (a2, b11, c6,d9), (a2, b11, c6, d10), (a2, b11, c6, d11), (a2, b11, c6, d12), (a2,b11, c7, d1), (a2, b11, c7, d2), (a2, b11, c7, d3), (a2, b11, c7, d4),(a2, b11, c7, d5), (a2, b11, c7, d6), (a2, b11, c7, d7), (a2, b11, c7,d8), (a2, b11, c7, d9), (a2, b11, c7, d10), (a2, b11, c7, d11), (a2,b11, c7, d12), (a2, b11, c8, d1), (a2, b11, c8, d2), (a2, b11, c8, d3),(a2, b11, c8, d4), (a2, b11, c8, d5), (a2, b11, c8, d6), (a2, b11, c8,d7), (a2, b11, c8, d8), (a2, b11, c8, d9), (a2, b11, c8, d10), (a2, b11,c8, d11), (a2, b11, c8, d12), (a2, b11, c9, d1), (a2, b11, c9, d2), (a2,b11, c9, d3), (a2, b11, c9, d4), (a2, b11, c9, d5), (a2, b11, c9, d6),(a2, b11, c9, d7), (a2, b11, c9, d8), (a2, b11, c9, d9), (a2, b11, c9,d10), (a2, b11, c9, d11), (a2, b11, c9, d12), (a2, b11, c10, d1), (a2,b11, c10, d2), (a2, b11, c10, d3), (a2, b11, c0, d4), (a2, b11, c10,d5), (a2, b11, c10, d6), (a2, b11, c10, d7), (a2, b11, c10, d8), (a2,b11, c10, d9), (a2, b11, c10, d10), (a2, b11, c10, d11), (a2, b11, c10,d12), (a2, 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(a4, b13, c4, d4), (a4, b13, c4, d5), (a4, b13, c4, d6),(a4, b13, c4, d7), (a4, b13, c4, d8), (a4, b13, c4, d9), (a4, b13, c4,d10), (a4, b13, c4, d11), (a4, b13, c4, d12), (a4, b13, c5, d1), (a4,b13, c5, d2), (a4, b13, c5, d3), (a4, b13, c5, d4), (a4, b13, c5, d5),(a4, b13, c5, d6), (a4, b13, c5, d7), (a4, b13, c5, d8), (a4, b13, c5,d9), (a4, b13, c5, d10), (a4, b13, c5, d11), (a4, b13, c5, d12), (a4,b13, c6, d1), (a4, b13, c6, d2), (a4, b13, c0, d3), (a4, b13, c0, d4),(a4, b13, c6, d5), (a4, b13, c6, d6), (a4, b13, c6, d7), (a4, b13, c0,d8), (a4, b13, c0, d9), (a4, b13, c6, d10), (a4, b13, c10, d11), (a4,b13, c6, d12), (a4, b13, c7, d1), (a4, b13, c7, d2), (a4, b13, c7, d3),(a4, b13, c7, d4), (a4, b13, c7, d5), (a4, b13, c7, d6), (a4, b13, c7,d7), (a4, b13, c7, d8), (a4, b13, c7, d9), (a4, b13, c7, d10), (a4, b13,c7, d11), (a4, b13, c7, d12), (a4, b13, c8, d1), (a4, b13, c8, d2), (a4,b13, c8, d3), (a4, b13, c8, d4), (a4, b13, c8, d5), (a4, b13, c8, d6),(a4, b13, c8, d7), (a4, b13, c8, d8), (a4, b13, c8, d9), (a4, b13, c8,d10), (a4, b13, c8, d11), (a4, b13, c8, d12), (a4, b13, c9, d1), (a4,b13, c9, d2), (a4, b13, c9, d3), (a4, b13, c9, d4), (a4, b13, c9, d5),(a4, b13, c9, d6), (a4, b13, c9, d7), (a4, b13, c9, d8), (a4, b13, c9,d9), (a4, b13, c9, d10), (a4, b13, c9, d11), (a4, b13, c9, d12), (a4,b13, c10, d1), (a4, b13, c10, d2), (a4, b13, c10, d3), (a4, b13, c10,d4), (a4, b13, c10, d5), (a4, b13, c10, d6), (a4, b13, c10, d7), (a4,b13, c10, d8), (a4, b13, c10, d9), (a4, b13, c10, d10), (a4, b13, c10,d11), (a4, b13, c10, d12), (a4, b13, c11, d1), (a4, b13, c11, d2), (a4,b13, c11, d3), (a4, b13, c11, d4), (a4, b13, c11, d5), (a4, b13, c11,d6), (a4, b13, c11, d7), (a4, b13, c11, d8), (a4, b13, c11, d9), (a4,b13, c11, d10), (a4, b13, c11, d11), (a4, b13, c11, d12), (a4, b13, c12,d1), (a4, b13, c12, d2), (a4, b13, c12, d3), (a4, b13, c12, d4), (a4,b13, c12, d5), (a4, b13, c12, d6), (a4, b13, c12, d7), (a4, b13, c12,d8), (a4, b13, c12, d9), (a4, b13, c12, d10), (a4, b13, c12, d11), (a4,b13, c12, d12), (a4, b13, c13, d1), (a4, b13, c13, d2), (a4, b13, c13,d3), (a4, b13, c13, d4), (a4, b13, c13, d5), (a4, b13, c13, d6), (a4,b13, c13, d7), (a4, b13, c13, d8), (a4, b13, c13, d9), (a4, b13, c13,d10), (a4, b13, c13, d11), (a4, b13, c13, d12), (a4, b14, c1, d1), (a4,b14, c1, d2), (a4, b14, c1, d3), (a4, b14, c1, d4), (a4, b14, c1, d5),(a4, b14, c1, d6), (a4, b14, c1, d7), (a4, b14, c1, d8), (a4, b14, c1,d9), (a4, b14, c1, d10), (a4, b14, c1, d11), (a4, b14, c1, d12), (a4,b14, c2, d1), (a4, b14, c2, d2), (a4, b14, c2, d3), (a4, b14, c2, d4),(a4, b14, c2, d5), (a4, b14, c2, d6), (a4, b14, c2, d7), (a4, b14, c2,d8), (a4, b14, c2, d9), (a4, b14, c2, d10), (a4, b14, c2, d11), (a4,b14, c2, d12), (a4, b14, c3, d1), (a4, b14, c3, d2), (a4, b14, c3, d3),(a4, b14, c3, d4), (a4, b14, c3, d5), (a4, b14, c3, d6), (a4, b14, c3,d7), (a4, b14, c3, d8), (a4, b14, c3, d9), (a4, b14, c3, d10), (a4, b14,c3, d11), (a4, b14, c3, d12), (a4, b14, c4, d1), (a4, b14, c4, d2), (a4,b14, c4, d3), (a4, b14, c4, d4), (a4, b14, c4, d5), (a4, b14, c4, d6),(a4, b14, c4, d7), (a4, b14, c4, d8), (a4, b14, c4, d9), (a4, b14, c4,d10), (a4, b14, c4, d11), (a4, b14, c4, d12), (a4, b14, c5, d1), (a4,b14, c5, d2), (a4, b14, c5, d3), (a4, b14, c5, d4), (a4, b14, c5, d5),(a4, b14, c5, d6), (a4, b14, c5, d7), (a4, b14, c5, d8), (a4, b14, c5,d9), (a4, b14, c5, d10), (a4, b14, c5, d11), (a4, b14, c5, d12), (a4,b14, c6, d1), (a4, b14, c6, d2), (a4, b14, c6, d3), (a4, b14, c6, d4),(a4, b14, c6, d5), (a4, b14, c6, d6), (a4, b14, c6, d7), (a4, b14, c6,d8), (a4, b14, c6, d9), (a4, b14, c6, d10), (a4, b14, c6, d11), (a4,b14, c6, d12), (a4, b14, c7, d1), (a4, b14, c7, d2), (a4, b14, c7, d3),(a4, b14, c7, d4), (a4, b14, c7, d5), (a4, b14, c7, d6), (a4, b14, c7,d7), (a4, b14, c7, d8), (a4, b14, c7, d9), (a4, b14, c7, d10), (a4, b14,c7, d11), (a4, b14, c7, d12), (a4, b14, c8, d1), (a4, b14, c8, d2), (a4,b14, c8, d3), (a4, b14, c8, d4), (a4, b14, c8, d5), (a4, b14, c8, d6),(a4, b14, c8, d7), (a4, b14, c8, d8), (a4, b14, c8, d9), (a4, b14, c8,d10), (a4, b14, c8, d11), (a4, b14, c8, d12), (a4, b14, c9, d1), (a4,b14, c9, d2), (a4, b14, c9, d3), (a4, b14, c9, d4), (a4, b14, c9, d5),(a4, b14, c9, d6), (a4, b14, c9, d7), (a4, b14, c9, d8), (a4, b14, c9,d9), (a4, b14, c9, d10), (a4, b14, c9, d11), (a4, b14, c9, d12), (a4,b14, c10, d1), (a4, b14, c10, d2), (a4, b14, c10, d3), (a4, b14, c10,d4), (a4, b14, c10, d5), (a4, b14, c10, d6), (a4, b14, c10, d7), (a4,b14, c10, d8), (a4, b14, c10, d9), (a4, b14, c10, d10), (a4, b14, c10,d11), (a4, b14, c10, d12), (a4, b14, c11, d1), (a4, b14, c11, d2), (a4,b14, c11, d3), (a4, b14, c11, d4), (a4, b14, c11, d5), (a4, b14, c11,d6), (a4, b14, c11, d7), (a4, b14, c11, d8), (a4, b14, c11, d9), (a4,b14, c1, d10), (a4, b14, c11, d11), (a4, b14, c1, d12), (a4, b14, c12,d1), (a4, b14, c12, d2), (a4, b14, c12, d3), (a4, b14, c12, d4), (a4,b14, c12, d5), (a4, b14, c12, d6), (a4, b14, c12, d7), (a4, b14, c12,d8), (a4, b14, c12, d9), (a4, b14, c12, d10), (a4, b14, c12, d11), (a4,b14, c12, d12), (a4, b14, c13, d1), (a4, b14, c13, d2), (a4, b14, c13,d3), (a4, b14, c13, d4), (a4, b14, c13, d5), (a4, b14, c13, d6), (a4,b14, c13, d7), (a4, b14, c13, d8), (a4, b14, c13, d9), (a4, b14, c13,d10), (a4, b14, c13, d11), (a4, b14, c13, d12), (a4, b15, c1, d1), (a4,b15, c1, d2), (a4, b15, c1, d3), (a4, b15, c1, d4), (a4, b15, c1, d5),(a4, b15, c1, d6), (a4, b15, c1, d7), (a4, b15, c1, d8), (a4, b15, c1,d9), (a4, b15, c1, d10), (a4, b15, c, d11), (a4, b15, c1, d12), (a4,b15, c2, d1), (a4, b15, c2, d2), (a4, b15, c2, d3), (a4, b15, c2, d4),(a4, b15, c2, d5), (a4, b15, c2, d6), (a4, b15, c2, d7), (a4, b15, c2,d8), (a4, b15, c2, d9), (a4, b15, c2, d10), (a4, b15, c2, d11), (a4,b15, c2, d12), (a4, b15, c3, d1), (a4, b15, c3, d2), (a4, b15, c3, d3),(a4, b15, c3, d4), (a4, b15, c3, d5), (a4, b15, c3, d6), (a4, b15, c3,d7), (a4, b15, c3, d8), (a4, b15, c3, d9), (a4, b15, c3, d10), (a4, b15,c3, d11), (a4, b15, c3, d12), (a4, b15, c4, d1), (a4, b15, c4, d2), (a4,b15, c4, d3), (a4, b15, c4, d4), (a4, b15, c4, d5), (a4, b15, c4, d6),(a4, b15, c4, d7), (a4, b15, c4, d8), (a4, b15, c4, d9), (a4, b15, c4,d10), (a4, b15, c4, d11), (a4, b15, c4, d12), (a4, b15, c5, d1), (a4,b15, c5, d2), (a4, b15, c5, d3), (a4, b15, c5, d4), (a4, b15, c5, d5),(a4, b15, c5, d6), (a4, b15, c5, d7), (a4, b15, c5, d8), (a4, b15, c5,d9), (a4, b15, c5, d10), (a4, b15, c5, d11), (a4, b15, c5, d12), (a4,b15, c6, d1), (a4, b15, c6, d2), (a4, b15, c6, d3), (a4, b15, c6, d4),(a4, b15, c6, d5), (a4, b15, c6, d6), (a4, b15, c6, d7), (a4, b15, c6,d8), (a4, b15, c6, d9), (a4, b15, c6, d10), (a4, b15, c6, d11), (a4,b15, c6, d12), (a4, b15, c7, d1), (a4, b15, c7, d2), (a4, b15, c7, d3),(a4, b15, c7, d4), (a4, b15, c7, d5), (a4, b15, c7, d6), (a4, b15, c7,d7), (a4, b15, c7, d8), (a4, b15, c7, d9), (a4, b15, c7, d10), (a4, b15,c7, d11), (a4, b15, c7, d12), (a4, b15, c8, d1), (a4, b15, c8, d2), (a4,b15, c8, d3), (a4, b15, c8, d4), (a4, b15, c8, d5), (a4, b15, c8, d6),(a4, b15, c8, d7), (a4, b1, c8, d8), (a4, b15, c8, d9), (a4, b15, c8,d10), (a4, b15, c8, d11), (a4, b15, c8, d12), (a4, b15, c9, d1), (a4,b15, c9, d2), (a4, b15, c9, d3), (a4, b15, c9, d4), (a4, b15, c9, d5),(a4, b15, c9, d6), (a4, b15, c9, d7), (a4, b15, c9, d8), (a4, b15, c9,d9), (a4, b15, c9, d10), (a4, b15, c9, d11)₇ (a4, b15, c9, d12), (a4,b15, c10, d1), (a4, b15, c10, d2), (a4, b15, c10, d3), (a4, b15, c10,d4), (a4, b15, c10, d5), (a4, b15, c10, d6), (a4, b15, c10, d7), (a4,b15, c10, d8), (a4, b15, c10, d9), (a4, b15, c10, d10), (a4, b15, c10,d11), (a4, b15, c10, d12), (a4, b15, c11, d1), (a4, b15, c11, d2), (a4,b15, c11, d3), (a4, b15, c11, d4), (a4, b15, c11, d5), (a4, b15, c11,d6), (a4, b15, c11, d7), (a4, b15, c11, d8), (a4, b15, c11, d9), (a4,b15, c11, d10), (a4, b15, c11, d11), (a4, b15, c11, d12), (a4, b15, c12,d1), (a4, b15, c12, d2), (a4, b15, c12, d3), (a4, b15, c12, d4), (a4,b15, c12, d5), (a4, b15, c12, d6), (a4, b15, c12, d7), (a4, b15, c12,d8), (a4, b15, c12, d9), (a4, b15, c12, d10), (a4, b15, c12, d11), (a4,b15, c12, d12), (a4, b15, c13, d1), (a4, b15, c13, d2), (a4, b15, c13,d3), (a4, b15, c13, d4), (a4, b15, c13, d5), (a4, b15, c13, d6), (a4,b15, c13, d7), (a4, b15, c13, d8), (a4, b15, c13, d9), (a4, b15, c13,d10), (a4, b15, c13, d11), (a4, b15, c13, d12), (a5, b1, c1, d1), (a5,b1, c1, d2), (a5, b1, c1, d3), (a5, b1, c1, d4), (a5, b1, c1, d5), (a5,b1, c1, d6), (a5, b1, c1, d7), (a5, b1, c1, d8), (a5, b1, c1, d9), (a5,b1, c1, d10), (a5, b1, c1, d11), (a5, b1, c1, d12), (a5, b1, c2, d1),(a5, b1, c2, d2), (a5, b1, c2, d3), (a5, b1, c2, d4), (a5, b1, c2, d5),(a5, b1, c2, d6), (a5, b1, c2, d7), (a5, b1, c2, d8), (a5, b1, c2, d9),(a5, b1, c2, d10), (a5, b1, c2, d11), (a5, b1, c2, d12), (a5, b1, c3,d1), (a5, b1, c3, d2), (a5, b1, c3, d3), (a5, b1, c3, d4), (a5, b1, c3,d5), (a5, b1, c3, d6), (a5, b1, c3, d7), (a5, b1, c3, d8), (a5, b1, c3,d9), (a5, b1, c3, d10), (a5, b1, c3, d11), (a5, b1, c3, d12), (a5, b1,c4, d1), (a5, b1, c4, d2), (a5, b1, c4, d3), (a5, b1, c4, d4), (a5, b1,c4, d5), (a5, b1, c4, d6), (a5, b1, c4, d7), (a5, b1, c4, d8), (a5, b1,c4, d9), (a5, b1, c4, d10), (a5, b1, c4, d11), (a5, b1, c4, d12), (a5,b1, c5, d1), (a5, b1, c5, d2), (a5, b1, c5, d3), (a5, b1, c5, d4), (a5,b1, c5, d5), (a5, b1, c5, d6), (a5, b1, c5, d7), (a5, b1, c5, d8), (a5,b1, c5, d9), (a5, b1, c5, d10), (a5, b1, c5, d11), (a5, b1, c5, d12),(a5, b1, c6, d1), (a5, b1, c6, d2), (a5, b1, c6, d3), (a5, b1, c6, d4),(a5, b1, c6, d5), (a5, b1, c6, d6), (a5, b1, c6, d7), (a5, b1, c6, d8),(a5, b1, c6, d9), (a5, b1, c6, d10), (a5, b1, c6, d11), (a5, b1, c6,d12), (a5, b1, c7, d1), (a5, b1, c7, d2), (a5, b1, c7, d3), (a5, b1, c7,d4), (a5, b1, c7, d5), (a5, b1, c7, d6), (a5, b1, c7, d7), (a5, b1, c7,d8), (a5, b1, c7, d9), (a5, b1, c7, d10), (a5, b1, c7, d11), (a5, b1,c7, d12), (a5, b1, c8, d1), (a5, b1, c8, d2), (a5, b1, c8, d3), (a5, b1,c8, d4), (a5, b1, c8, d5), (a5, b1, c8, d6), (a5, b1, c8, d7), (a5, b1,c8, d8), (a5, b1, c8, d9), (a5, b1, c8, d10), (a5, b1, c8, d11), (a5,b1, c8, d12), (a5, b1, c9, d1), (a5, b1, c9, d2), (a5, b1, c9, d3), (a5,b1, c9, d4), (a5, b1, c9, d5), (a5, b1, c9, d6), (a5, b1, c9, d7), (a5,b1, c9, d8), (a5, b1, c9, d9), (a5, b1, c9, d10), (a5, b1, c9, d11),(a5, b1, c9, d12), (a5, b1, c10, d1), (a5, b1, c10, d2), (a5, b1, c10,d3), (a5, b1, c10, d4), (a5, b1, c10, d5), (a5, b1, c10, d6), (a5, b1,c10, d7), (a5, b1, c10, d8), (a5, b1, c10, d9), (a5, b1, c10, d10), (a5,b1, c10, d11), (a5, b1, c10, d12), (a5, b1, c11, d1), (a5, b1, c11, d2),(a5, b1, c11, d3), (a5, b1, c11, d4), (a5, b1, c11, d5), (a5, b1, c11,d6), (a5, b1, c11, d7), (a5, b1, c11, d8), (a5, b1, c11, d9), (a5, b1,c11, d10), (a5, b1, c11, d11), (a5, b1, c11, d12), (a5, b1, c12, d1),(a5, b1, c12, d2), (a5, b1, c12, d3), (a5, b1, c12, d4), (a5, b1, c12,d5), (a5, b1, c12, d6), (a5, b1, c12, d7), (a5, b1, c12, d8), (a5, b1,c12, d9), (a5, b1, c12, d10), (a5, b1, c12, d11), (a5, b1, c12, d12),(a5, b1, c13, d1), (a5, b1, c13, d2), (a5, b1, c13, d3), (a5, b1, c13,d4), (a5, b1, 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(a6, b12, c1, d10), (a6, b12, c1, d11), (a6, b12, c1, d12), (a6,b12, c2, d1), (a6, b12, c2, d2), (a6, b12, c2, d3), (a6, b12, c2, d4),(a6, b12, c2, d5), (a6, b12, c2, d6), (a6, b12, c2, d7), (a6, b12, c2,d8), (a6, b12, c2, d9), (a6, b12, c2, d10), (a6, b12, c2, d11), (a6,b12, c2, d12), (a6, b12, c3, d1), (a6, b12, c3, d2), (a6, b12, c3, d3),(a6, b12, c3, d4), (a6, b12, c3, d5), (a6, b12, c3, d6), (a6, b12, c3,d7), (a6, b12, c3, d8), (a6, b12, c3, d9), (a6, b12, c3, d10), (a6, b12,c3, d11), (a6, b12, c3, d12), (a6, b12, c4, d1), (a6, b12, c4, d2), (a6,b12, c4, d3), (a6, b12, c4, d4), (a6, b12, c4, d5), (a6, b12, c4, d6),(a6, b12, c4, d7), (a6, b12, c4, d8), (a6, b12, c4, d9), (a6, b12, c4,d10), (a6, b12, c4, d11), (a6, b12, c4, d12), (a6, b12, c5, d1), (a6,b12, c5, d2), (a6, b12, c5, d3), (a6, b12, c5, d4), (a6, b12, c5, d5),(a6, b12, c5, d6), (a6, b12, c5, d7), (a6, b12, c5, d8), (a6, b12, c5,d9), (a6, b12, c5, d10), (a6, b12, c5, d11), (a6, b12, c5, d12), (a6,b12, c6, d1), (a6, b12, c6, d2), (a6, b12, c6, d3), (a6, b12, c6, d4),(a6, b12, c6, d5), (a6, b12, c6, d6), (a6, b12, c6, d7), (a6, b12, c6,d8), (a6, b12, c6, d9), (a6, b12, c6, d10), (a6, b12, c6, d11), (a6,b12, c6, d12), (a6, b12, c7, d1), (a6, b12, c7, d2), (a6, b12, c7, d3),(a6, b12, c7, d4), (a6, b12, c7, d5), (a6, b12, c7, d6), (a6, b12, c7,d7), (a6, b12, c7, d8), (a6, b12, c7, d9), (a6, b12, c7, d10), (a6, b12,c7, d11), (a6, b12, c7, d12), (a6, b12, c8, d1), (a6, b12, c8, d2), (a6,b12, c8, d3), (a6, b12, c8, d4), (a6, b12, c8, d5), (a6, b12, c8, d6),(a6, b12, c8, d7), (a6, b12, c8, d8), (a6, b12, c8, d9), (a6, b12, c8,d10), (a6, b12, c8, d11), (a6, b12, c8, d12), (a6, b12, c9, d1), (a6,b12, c9, d2), (a6, b12, c9, d3), (a6, b12, c9, d4), (a6, b12, c9, d5),(a6, b12, c9, d6), (a6, b12, c9, d7), (a6, b12, c9, d8), (a6, b12, c9,d9), (a6, b12, c9, d10), (a6, b12, c9, d11), (a6, b12, c9, d12), (a6,b12, c10, d1), (a6, b12, c10, d2), (a6, b12, c0, d3), (a6, b12, c10,d4), (a6, b12, c10, d5), (a6, b12, c10, d6), (a6, b12, c0, d7), (a6,b12, c0, d8), (a6, b12, c10, d9), (a6, b12, c10, d10), (a6, b12, c10,d11), (a6, b12, c10, d12), (a6, b12, c11, d1), (a6, b12, c11, d2), (a6,b12, c11, d3), (a6, b12, c11, d4), (a6, b12, c11, d5), (a6, b12, c11,d6), (a6, b12, c11, d7), (a6, b12, c11, d8), (a6, b12, c11, d9), (a6,b12, c11, d10), (a6, b12, c11, d11), (a6, b12, c11, d12), (a6, b12, c12,d1), (a6, b12, c12, d2), (a6, b12, c12, d3), (a6, b12, c12, d4), (a6,b12, c12, d5), (a6, b12, c12, d6), (a6, b12, c12, d7), (a6, b12, c12,d8), (a6, b12, c12, d9), (a6, b12, c12, d10), (a6, b12, c12, d11), (a6,b12, c12, d12), (a6, b12, c13, d1), (a6, b12, c13, d2), (a6, b12, c13,d3), (a6, b12, c13, d4), (a6, b12, c13, d5), (a6, b12, c13, d6), (a6,b12, c13, d7), (a6, b12, c13, d8), (a6, b12, c13, d9), (a6, b12, c13,d10), (a6, b12, c13, d11), (a6, b12, c13, d12), (a6, b13, c1, d1), (a6,b13, c1, d2), (a6, b13, c1, d3), (a6, b13, c1, d4), (a6, b13, c1, d5),(a6, b13, c1, d6), (a6, b13, c1, d7), (a6, b13, c1, d8), (a6, b13, c1,d9), (a6, b13, c1, d10), (a6, b13, c1, d11), (a6, b13, c1, d12), (a6,b13, c2, d1), (a6, b13, c2, d2), (a6, b13, c2, d3), (a6, b13, c2, d4),(a6, b13, c2, d5), (a6, b13, c2, d6), (a6, b13, c2, d7), (a6, b13, c2,d8), (a6, b13, c2, d9), (a6, b13, c2, d10), (a6, b13, c2, d11), (a6,b13, c2, d12), (a6, b13, c3, d1), (a6, b13, c3, d2), (a6, b13, c3, d3),(a6, b13, c3, d4), (a6, b13, c3, d5), (a6, b13, c3, d6), (a6, b13, c3,d7), (a6, b13, c3, d8), (a6, b13, c3, d9), (a6, b13, c3, d10), (a6, b13,c3, d11), (a6, b13, c3, d12), (a6, b13, c4, d1), (a6, b13, c4, d2), (a6,b13, c4, d3), (a6, b13, c4, d4), (a6, b13, c4, d5), (a6, b13, c4, d6),(a6, b13, c4, d7), (a6, b13, c4, d8), (a6, b13, c4, d9), (a6, b13, c4,d10), (a6, b13, c4, d11), (a6, b13, c4, d12), (a6, b13, c6, d1), (a6,b13, c6, d2), (a6, b13, c5, d3), (a6, b13, c5, d4), (a6, b13, c5, d5),(a6, b13, c5, d6), (a6, b13, c5, d7), (a6, b13, c6, d8), (a6, b13, c5,d9), (a6, b13, c5, d10), (a6, b13, c5, d11), (a6, b13, c5, d12), (a6,b13, c6, d1), (a6, b13, c6, d2), (a6, b13, c6, d3), (a6, b13, c6, d4),(a6, b13, c6, d5), (a6, b13, c6, d6), (a6, b13, c6, d7), (a6, b13, c6,d8), (a6, b13, c6, d9), (a6, b13, c6, d10), (a6, b13, c6, d11), (a6,b13, c6, d12), (a6, b13, c7, d1), (a6, b13, c7, d2), (a6, b13, c7, d3),(a6, b13, c7, d4), (a6, b13, c7, d5), (a6, b13, c7, d6), (a6, b13, c7,d7), (a6, b13, c7, d8), (a6, b13, c7, d9), (a6, b13, c7, d10), (a6, b13,c7, d11), (a6, b13, c7, d12), (a6, b13, c8, d1), (a6, b13, c8, d2), (a6,b13, c8, d3), (a6, b13, c8, d4), (a6, b13, c8, d5), (a6, b13, c8, d6),(a6, b13, c8, d7), (a6, b13, c8, d8), (a6, b13, c8, d9), (a6, b13, c8,d10), (a6, b13, c8, d1), (a6, b13, c8, d12), (a6, b13, c9, d1), (a6,b13, c9, d2), (a6, b13, c9, d3), (a6, b13, c9, d4), (a6, b13, c9, d5),(a6, b13, c9, d6), (a6, b13, c9, d7), (a6, b13, c9, d8), (a6, b13, c9,d9), (a6, b13, c9, d10), (a6, b13, c9, d11), (a6, b13, c9, d12), (a6,b13, c10, d1), (a6, b13, c10, d2), (a6, b13, c10, d3), (a6, b13, c10,d4), (a6, b13, c10, d5), (a6, b13, c10, d6), (a6, b13, c10, d7), (a6,b13, c10, d8), (a6, b13, c10, d9), (a6, b13, c10, d10), (a6, b13, c10,d11), (a6, b13, c10, d12), (a6, b13, c11, d1), (a6, b13, c11, d2), (a6,b13, c11, d3), (a6, b13, c11, d4), (a6, b13, c11, d5), (a6, b13, c11,d6), (a6, b13, c11, d7), (a6, b13, c11, d8), (a6, b13, c11, d9), (a6,b13, c11, d10), (a6, b13, c11, d11), (a6, b13, c11, d12), (a6, b13, c12,d1), (a6, b13, c12, d2), (a6, b13, c12, d3), (a6, b13, c12, d4), (a6,b13, c12, d5), (a6, b13, c12, d6), (a6, b13, c12, d7), (a6, b13, c12,d8), (a6, b13, c12, d9), (a6, b13, c12, d10), (a6, b13, c12, d11), (a6,b13, c12, d12), (a6, b13, c13, d1), (a6, b13, c13, d2), (a6, b13, c13,d3), (a6, b13, c13, d4), (a6, b13, c13, d5), (a6, b13, c13, d6), (a6,b13, c13, d7), (a6, b13, c13, d8), (a6, b13, c13, d9), (a6, b13, c13,d10), (a6, b13, c13, d11), (a6, b13, c13, d12), (a6, b14, c1, d1), (a6,b14, c1, d2), (a6, b14, c1, d3), (a6, b14, c1, d4), (a6, b14, c1, d5),(a6, b14, c1, d6), (a6, b14, c1, d7), (a6, b14, c1, d8), (a6, b14, c1,d9), (a6, b14, c1, d10), (a6, b14, c1, d11), (a6, b14, c1, d12), (a6,b14, c2, d1), (a6, b14, c2, d2), (a6, b14, c2, d3), (a6, b14, c2, d4),(a6, b14, c2, d5), (a6, b14, c2, d6), (a6, b14, c2, d7), (a6, b14, c2,d8), (a6, b14, c2, d9), (a6, b14, c2, d10), (a6, b14, c2, d11), (a6,b14, c2, d12), (a6, b14, c3, d1), (a6, b14, c3, d2), (a6, b14, c3, d3),(a6, b14, c3, d4), (a6, b14, c3, d5), (a6, b14, c3, d6), (a6, b14, c3,d7), (a6, b14, c3, d8), (a6, b14, c3, d9), (a6, b14, c3, d10), (a6, b14,c3, d11), (a6, b14, c3, d12), (a6, b14, c4, d1), (a6, b14, c4, d2), (a6,b14, c4, d3), (a6, b14, c4, d4), (a6, b14, c4, d5), (a6, b14, c4, d6),(a6, b14, c4, d7), (a6, b14, c4, d8), (a6, b14, c4, d9), (a6, b14, c4,d10), (a6, b14, c4, d11), (a6, b14, c4, d12), (a6, b14, c5, d1), (a6,b14, c5, d2), (a6, b14, c5, d3), (a6, b14, c5, d4), (a6, b14, c5, d5),(a6, b14, c5, d6), (a6, b14, c5, d7), (a6, b14, c5, d8), (a6, b14, c5,d9), (a6, b14, c5, d10), (a6, b14, c5, d11), (a6, b14, c5, d12), (a6,b14, c6, d1), (a6, b14, c6, d2), (a6, b14, c6, d3), (a6, b14, c6, d4),(a6, b14, c6, d5), (a6, b14, c6, d6), (a6, b14, c6, d7), (a6, b14, c6,d8), (a6, b14, c6, d9), (a6, b14, c6, d10), (a6, b14, c6, d11), (a6,b14, c6, d12), (a6, b14, c7, d1), (a6, b14, c7, d2), (a6, b14, c7, d3),(a6, b14, c7, d4), (a6, b14, c7, d5), (a6, b14, c7, d6), (a6, b14, c7,d7), (a6, b14, c7, d8), (a6, b14, c7, d9), (a6, b14, c7, d10), (a6, b14,c7, d11), (a6, b14, c7, d12), (a6, b14, c8, d1), (a6, b14, c8, d2), (a6,b14, c8, d3), (a6, b14, c8, d4), (a6, b14, c8, d5), (a6, b14, c8, d6),(a6, b14, c8, d7), (a6, b14, c8, d8), (a6, b14, c8, d9), (a6, b14, c8,d10), (a6, b14, c8, d11), (a6, b14, c8, d12), (a6, b14, c9, d1), (a6,b14, c9, d2), (a6, b14, c9, d3), (a6, b14, c9, d4), (a6, b14, c9, d5),(a6, b14, c9, d6), (a6, b14, c9, d7), (a6, b14, c9, d8), (a6, b14, c9,d9), (a6, b14, c9, d10), (a6, b14, c9, d11), (a6, b14, c9, d12), (a6,b14, c10, d1), (a6, b14, c10, d2), (a6, b14, c10, d3), (a6, b14, c10,d4), (a6, b14, c10, d5), (a6, b14, c10, d6), (a6, b14, c10, d7), (a6,b14, c10, d8), (a6, b14, c10, d9), (a6, b14, c10, d10), (a6, b14, c10,d11), (a6, b14, c10, d12), (a6, b14, c11, d1), (a6, b14, c11, d2), (a6,b14, c11, d3), (a6, b14, c11, d4), (a6, b14, c11, d5), (a6, b14, c11,d6), (a6, b14, c11, d7), (a6, b14, c11, d8), (a6, b14, c11, d9), (a6,b14, c11, d10), (a6, b14, c11, d11), (a6, b14, c11, d12), (a6, b14, c12,d1), (a6, b14, c12, d2)₇ (a6, b14, c12, d3), (a6, b14, c12, d4), (a6,b14, c12, d5), (a6, b14, c12, d6), (a6, b14, c12, d7), (a6, b14, c12,d8), (a6, b14, c12, d9), (a6, b14, c12, d10), (a6, b14, c12, d11), (a6,b14, c12, d12), (a6, b14, c13, d1), (a6, b14, c13, d2), (a6, b14, c13,d3), (a6, b14, c13, d4), (a6, b14, c13, d5), (a6, b14, c13, d6), (a6,b14, c13, d7), (a6, b14, c13, d8), (a6, b14, c13, d9), (a6, b14, c13,d10), (a6, b14, c13, d11), (a6, b14, c13, d12), (a6, b15, c1, d1), (a6,b15, c1, d2), (a6, b15, c1, d3), (a6, b15, c1, d4), (a6, b15, c1, d5),(a6, b15, c1, d6), (a6, b15, c1, d7), (a6, b15, c1, d8), (a6, b15, c1,d9), (a6, b15, c1, d10), (a6, b15, c1, d11), (a6, b15, c1, d12), (a6,b15, c2, d1), (a6, b15, c2, d2), (a6, b15, c2, d3), (a6, b15, c2, d4),(a6, b15, c2, d5), (a6, b15, c2, d6), (a6, b15, c2, d7), (a6, b15, c2,d8), (a6, b15, c2, d9), (a6, b15, c2, d10), (a6, b15, c2, d11), (a6,b15, c2, d12), (a6, b15, c3, d1), (a6, b15, c3, d2), (a6, b15, c3, d3),(a6, b15, c3, d4), (a6, b15, c3, d5), (a6, b15, c3, d6), (a6, b15, c3,d7), (a6, b15, c3, d8), (a6, b15, c3, d9), (a6, b15, c3, d10), (a6, b15,c3, d11), (a6, b15, c3, d12), (a6, b15, c4, d1), (a6, b15, c4, d2), (a6,b15, c4, d3), (a6, b15, c4, d4), (a6, b15, c4, d5), (a6, b15, c4, d6),(a6, b15, c4, d7), (a6, b15, c4, d8), (a6, b15, c4, d9), (a6, b15, c4,d10), (a6, b15, c4, d11), (a6, b15, c4, d12), (a6, b15, c5, d1), (a6,b15, c5, d2), (a6, b15, c5, d3), (a6, b15, c5, d4), (a6, b15, c5, d5),(a6, b15, c5, d6), (a6, b15, c5, d7), (a6, b15, c5, d8), (a6, b15, c5,d9), (a6, b15, c5, d10), (a6, b15, c5, d11), (a6, b15, c5, d12), (a6,b15, c6, d1), (a6, b15, c6, d2), (a6, b15, c6, d3), (a6, b15, c6, d4),(a6, b15, c6, d5), (a6, b15, c6, d6), (a6, b15, c6, d7), (a6, b15, c6,d8), (a6, b15, c6, d9), (a6, b15, c6, d10), (a6, b15, c6, d11), (a6,b15, c6, d12), (a6, b15, c7, d1), (a6, b15, c7, d2), (a6, b15, c7, d3),(a6, b15, c7, d4), (a6, b15, c7, d5), (a6, b15, c7, d6), (a6, b15, c7,d7), (a6, b15, c7, d8), (a6, b15, c7, d9), (a6, b15, c7, d10), (a6, b15,c7, d11), (a6, b15, c7, d12), (a6, b15, c8, d1), (a6, b15, c5, d2), (a6,b15, c8, d3), (a6, b15, c5, d4), (a6, b15, c8, d5), (a6, b15, c8, d6),(a6, b15, c8, d7), (a6, b16, c8, d8), (a6, b15, c8, d9), (a6, b15, c8,d10), (a6, b15, c8, d11), (a6, b15, c8, d12), (a6, b15, c9, d1), (a6,b15, c9, d2), (a6, b15, c9, d3), (a6, b15, c9, d4), (a6, b15, c9, d5),(a6, b15, c9, d6), (a6, b15, c9, d7), (a6, b15, c9, d8), (a6, b15, c9,d9), (a6, b15, c9, d10), (a6, b15, c9, d11), (a6, b15, c9, d12), (a6,b15, c10, d1), (a6, b15, c10, d2), (a6, b15, c10, d3), (a6, b15, c10,d4), (a6, b15, c10, d5), (a6, b15, c10, d6), (a6, b15, c10, d7), (a6,b15, c10, d8), (a6, b15, c10, d9), (a6, b15, c10, d10), (a6, b15, c10,d11), (a6, b15, c10, d12), (a6, b15, c11, d1), (a6, b15, c11, d2), (a6,b15, c11, d3), (a6, b15, c11, d4), (a6, b15, c11, d5), (a6, b15, c11,d6), (a6, b15, c11, d7), (a6, b15, c11, d8), (a6, b15, c11, d9), (a6,b15, c11, d10), (a6, b15, c11, d11), (a6, b15, c11, d12), (a6, b15, c12,d1), (a6, b15, c12, d2), (a6, b15, c12, d3), (a6, b15, c12, d4), (a6,b15, c12, d5), (a6, b15, c12, d6), (a6, b15, c12, d7), (a6, b15, c12,d8), (a6, b15, c12, d9), (a6, b15, c12, d10), (a6, b15, c12, d11), (a6,b15, c12, d12), (a6, b15, c13, d1), (a6, b15, c13, d2), (a6, b15, c13,d3), (a6, b15, c13, d4), (a6, b15, c13, d5), (a6, b15, c13, d6), (a6,b15, c13, d7), (a6, b15, c13, d8), (a6, b15, c13, d9), (a6, b15, c13,d10), (a6, b15, c13, d11), (a6, b15, c13, d12) are synthesized.

Test Example 1 Preparation of MMP

Various human MMPs (MMP-2, MMP-9 and MMP-13) were purchased fromCalbiochem (EMD/MERCK Biosciences).

Since the purchased MMP-13 was Proenzyme, the activated one was used,which was incubated at 37° C. for 2 hours after the successive additionof an assay buffer (containing 50 mM Tris-HCl (pH7.6), 0.3 M NaCl, 10 mMCaCl₂, 0.005% Brij35) and APMA (final concentration 1 mM) to the enzymesolution.

Test Example 2 Method for Measuring Enzyme Inhibiting Activity ofVarious MMPs

The enzyme activity of MMPs was measured according to the methoddescribed in C. Graham Knight, Frances Willenbrock and Gillian Murphy: Anovel coumarin-labelled peptide for sensitive continuous assays of thematrix metalloproteinases: FEBS LETT., 296, (1992), 263-266. As asubstrate, MOCAc-Pro-Leu-Gly-Leu-A₂Pr(DNP)-Ala-Arg-NH₂ (PeptideInstitute, Inc. Osaka, Japan) was used, and the following four assaysare performed per compound (inhibitor) for measuring the inhibitingactivity.

(A) Substrate (synthetic substrate), enzyme (MMPs), inhibitor(B) Substrate (synthetic substrate), inhibitor(C) Substrate (synthetic substrate), enzyme (MMPs)(D) Substrate (synthetic substrate)In each assay, the fluorescent intensity was measured, and inhibition(%) was calculated by the following equation.

Inhibition(%)=[I−(A−B)/(C−D)]×100

IC₅₀ indicates a concentration at which inhibition (%) is 50%.

Inhibiting activity values for MMP-2, MMP-9 and MMP-13 measured by theaforementioned method are shown in Table 1.

TABLE 1 IC50 (uM) No MMP-2 MMP-9 MMP-13 I-1 >10 >10 0.121 I-5 >10 >100.110 I-11 >10 >10 0.0549 I-13 >10 >10 0.0443 I-15 1-10 >10 0.126I-19 >10 >10 0.142 I-20 1-10 >10 0.0945 I-21 >10 >10 0.176 I-24 >10 >100.138 I-25 >10 >10 0.145 I-27 >10 >10 0.0423 I-28 >10 >10 0.0771 I-321-10 >10 0.0685 I-45 1-10 >10 0.186 I-47 >10 >10 0.131 I-49 1-10 >100.0965 I-53 1-10 >10 0.107 I-66 >10 >10 0.0396

PREPARATION EXAMPLES Preparation Example 1

A granule containing the following ingredients is produced.

Ingredient Active ingredient 10 mg Lactose 700 mg Corn starch 274 mgHPC-L 16 mg 1000 mg

The active ingredient and lactose are passed through a 60 mesh sieve.Corn starch is passed through a 120 mesh sieve. These are mixed by aV-type mixing machine. To the mixed powder is added a HPC-L (lowviscosity hydroxypropylcellulose) aqueous solution, the materials arekneaded, granulated (extrusion granulation, pore diameter 0.5-1 mm), anddried. The resulting dried granule is passed through a vibration sieve(12/60 mesh) to give a granule.

Preparation Examples 2

A filling powder into capsules, having the following ingredients, isproduced.

Ingredient Active ingredient 10 mg Lactose 79 mg Corn starch 10 mgMagnesium stearate 1 mg 100 mg

The active ingredient and lactose are passed through a 60 mesh sieve.Corn starch is passed through a 120 mesh sieve. These are mixed withmagnesium stearate are by a V-type mixing machine. The 10% powder, 100mg, is filled into a No. 5 hard-gelatin capsule.

Preparation Examples 3

A tablet having the following ingredients is produced.

Ingredient Active ingredient 10 mg Lactose 90 mg Microcrystallinecellulose 30 mg CMC-Na 15 mg Magnesium stearate 5 mg 150 mg

The active ingredient, lactose, microcrystalline cellulose, and CMC-Na(carboxymethylcellulose sodium salt) are passed through a 60 mesh sieve,and mixed. Magnesium stearate is mixed with the above powder to give themixed powder for preparing a tablet. The obtained mixed powder iscompressed to give a 150-mg tablet.

Preparation Example 4

An aerosol solution containing the following ingredients is produced.

Weight Active ingredient 0.25 Ethanol 25.75 Propellant 22(chlorodifluoromethane) 74.00 Total 100.00

The active ingredient and ethanol are mixed and added to a portion ofthe propellant 22. After being cooled to −30° C., the mixture istransferred to a filling device. Then, a required amount is supplied toa stainless steel container, and is diluted with a rest of propellant. Avalve unit is attached to the container.

Preparation Example 5

An intravenous preparation for vein is produced as follows:

Active ingredient 100 mg Physiological saline 1000 ml

A solution of the aforementioned ingredients is intravenouslyadministered to a patient usually at a rate of 1 ml per minutes.

Preparation Example 6

A transdermal preparation containing the following ingredients isproduced.

Active ingredient 10 mg Isopropyl myristate 990 mg 1000 mg

After the compound represented by the formula (I) is dispersed intoisopropyl myristate, the dispersion is mixed with an acryl-basedadhesive (e.g. Nicazol), and then a transdermal preparation was obtainedby applying to an application support.

Preparation Example 7

An ointment containing the following ingredients is produced.

Active ingredient 10 mg Liquid paraffin 75 mg White vaseline 925 mg 1000mg

The compound represented by the formula (I) and liquid paraffin aredispersed, and kneaded with white vaseline to give an ointment.

INDUSTRIAL APPLICABILITY

The sulfonamide derivatives having the MMP-13 selective inhibitingactivity of the present invention are useful as a medicine for treatingor preventing a disease associated with MMP-13, particularlyosteoarthritis.

1. A compound represented by the general formula (I):

wherein R¹ is optionally substituted aryl, optionally substitutedheteroaryl, an optionally substituted non-aromatic carbocyclic group, oran optionally substituted non-aromatic heterocyclic group; Z is —O—,—S—, —SO-7-SO₂—, —N(R¹¹)—, —N(R¹⁰)—C(═O)—, —C(═O)—N(R¹⁰)—, —N(R¹⁰)—SO₂—,—SO₂—N(R¹⁰)—, —C(═O)—, —O—C(═O)—, —C(═O)—O—, —N(R¹⁰)—C(═O)—N(R¹⁰)—,—N(R¹⁰)—C(═S)—N(R¹⁰)—, —O—N═C(R⁸)—, —C(R⁸)═N—O—, —O—C(═O)—N(R¹⁰)—,—N(R¹¹)—C(═O)—O—, —C(═O)C(═O)—, an optionally substituted non-aromaticcarbocyclic group, an optionally substituted non-aromatic heterocyclicgroup, C1-C5 alkylene which is optionally substituted and may beintervened with a substituent selected from Substituent group a, C1-C5alkenylene which is optionally substituted, and may be intervened with asubstituent selected from Substituent group a, or C1-C5 alkynylene whichis optionally substituted, and may be intervened with a substituentselected from Substituent group a, wherein the Substituent group aconsists of —O—, —S—, —SO—, —SO₂—, —N(R¹⁰)—, —N(R¹¹)—C(═O)—,—C(═O)—N(R¹⁰)—, —N(R¹⁰)—SO₂—, —SO₂—N(R¹⁰)—, —C(═O)—, —O—C(═O)—,—C(═O)—O—, —N(R¹⁰)—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═S)—N(R¹⁰)—, —O—N═C(R⁸)—,—C(R⁸)═N—O—, —O—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═O)—O—, and —C(═O)—C(═O)—, R⁸and R¹⁰ are each independently a hydrogen atom or lower alkyl; A is agroup represented by the formula;

wherein R⁶ and R⁷ are each independently halogen, lower alkyl,cycloalkyl, lower alkenyl, lower alkynyl, lower alkyloxy, loweralkenyloxy, lower alkylthio, halo lower alkyl, halo lower alkyloxy, halolower alkylthio, hydroxy, hydroxy lower alkyl, mercapto, carboxy, loweralkyloxycarbonyl, lower alkylsulfonyl, acyl, acyloxy, nitro, cyano,optionally substituted amino, or optionally substituted aminocarbonyl; Bring is a nitrogen-containing heterocycle optionally further containinga nitrogen atom, an oxygen atom, and/or a sulfur atom in the ring; m andn are each independently an integer of 0 to 3; R² is a hydrogen atom,optionally substituted lower alkyl, optionally substituted aralkyl,optionally substituted heteroarylalkyl, optionally substituted aryl, oroptionally substituted heteroaryl; R³ is a hydrogen atom, optionallysubstituted lower alkyl, optionally substituted aralkyl, optionallysubstituted heteroarylalkyl, optionally substituted aryl, or optionallysubstituted heteroaryl; R⁴ is a hydrogen atom, or R³ and R⁴ may be takentogether with an adjacent carbon atom to form a 5- to 6-memberednon-aromatic carbocyclic ring or a 5- to 6-membered non-aromaticheterocyclic ring; R⁵ is hydroxy, lower alkyloxy, or —NHOH; providedthat when B ring is piperazine and Z is —CH₂—O—, R¹ is not pyridyl, anoptically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.
 2. The compound according to claim 1, which isrepresented by the general formula (II):

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Z, m, n and B ring are as defined inclaim 1, an optically active isomer, a pharmaceutically acceptable salt,or a solvate thereof.
 3. The compound according to claim 1, which isrepresented by the general formula (III):

wherein R¹, R², R³, R⁴: R⁵, R⁶, R⁷, Z, m: n and B ring are as defined inclaim 1, an optically active isomer, a pharmaceutically acceptable salt,or a solvate thereof.
 4. The compound according to claim 1, wherein R¹is optionally substituted naphthyl or optionally substituted carbazolyl,an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.
 5. The compound according to claim 1, wherein R¹ is agroup represented by the formula:

wherein R²⁴ is a hydrogen atom; lower alkyl optionally substituted withcarboxy or lower alkyloxyimino; lower alkenyl optionally substitutedwith carboxy; hydroxy; lower alkyloxy optionally substituted withcycloalkyl, hydroxy, lower alkyloxy, carboxy, or aminocarbonyloptionally substituted with 1 or 2 lower alkyl(s); carboxy; acyl; aminooptionally substitute with 1 or 2 acyl(s) or lower alkylsulfonyl(s);aminocarbonyl optionally substituted with 1 or 2 lower alkyl(s); or anon-aromatic heterocycle; R²⁵ is halogen, cyano, or acyl; n¹ is aninteger of 0 to 2, and R²⁵ may be substituted on all replaceableconstituent carbon atoms, an optically active isomer, a pharmaceuticallyacceptable salt, or a solvate thereof.
 6. The compound according toclaim 1, wherein Z is —C(R⁸)(R⁹)—, —O—, —S—, —SO—, —SO₂—, —N(R¹⁰)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)═C(R⁹)—, —C≡C—, —O—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—O—, —S—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—S—, —SO—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—SO—, —SO₂—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—, —N(R¹⁰)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—N(R¹⁰)—, —N(R¹¹)—C(═O)—, —C(═O)—N(R¹⁰)—, —N(R¹⁰)—SO₂—,—SO₂—N(R¹⁰)—, —C(R⁸)(R⁹)—C(═O)—, —C(═O)—C(R¹⁰)(R⁹)—, —C(═O)—C(═O)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(R⁸)═C(R⁹)—,—C(R⁸)═C(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C≡C—, —C≡C—C(R⁸)(R⁹)—,—O—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—O—C(R⁸) (R⁹)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—O—, —S—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—S—, —SO—C(R⁸)(R⁹)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—SO—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—SO—,—SO₂—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—SO₂—, —N(R¹⁰)—C(R⁸)(R⁹)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—N(R¹⁰)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(R⁸)(R⁹)—N(R¹¹)—,—C(═O)—C(R⁸)(R⁹)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(═O)—C(R⁸)(R⁹)—,—C(R⁸)(R⁹)—C(R⁸)(R⁹)—C(═O)—, —C(R⁸)(R⁹)—N(R¹⁰)—, —C(═O)—,—N(R¹⁰)—C(═O)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(═O)—N(R¹⁰)—,—C(═O)—N(R¹⁰)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—N(R¹⁰)—SO₂—,—N(R¹⁰)—SO₂—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—SO₂—N(R¹⁰)—, —SO₂—N(R¹⁰)—C(R⁸)(R⁹)—,—N(R¹⁰)—C(═O)—N(R¹⁰)—, —N(R¹⁰)—C(═S)—N(R¹⁰)—, —O—N═C(R⁸)—, —C(R⁸)═N—O—,—O—C(═O)—C(R⁸)(R⁹)—, —C(R⁸)(R⁹)—C(═O)—O—, —O—C(═O)—N(R¹⁰)—, or—N(R¹⁰)—C(═O)—O—, wherein R⁸, R⁹ and R¹⁰ are each independently ahydrogen atom or lower alkyl, an optically active isomer, apharmaceutically acceptable salt, or a solvate thereof.
 7. The compoundaccording to claim 1, wherein a group represented by the formula:

is a group represented by the formula:

wherein X is a carbon atom or a nitrogen atom, C ring is a 5- to8-membered nitrogen-containing heterocycle, and R⁷ and m are as definedin claim 1, an optically active isomer, a pharmaceutically acceptablesalt, or a solvate thereof.
 8. The compound according to claim 1,wherein R² is a hydrogen atom, an optically active isomer, apharmaceutically acceptable salt, or a solvate thereof.
 9. The compoundaccording to claim 1, wherein R³ is a hydrogen atom, methyl, ethyl,n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, hydroxymethyl,1-hydroxyethyl, 2-hydroxyethyl, carboxymethyl, carboxyethyl,methyloxymethyl, methylthiomethyl, 2-methylthioethyl, phenyl,4-hydroxyphenyl, 4-fluorophenyl, 4-methyloxyphenyl, benzyl,4-hydroxybenzyl, 4-fluorobenzyl, 4-chlorobenzyl, 4-methoxybenzyl,indol-3-ylmethyl, 1-carboxymethylindol-3-ylmethyl, thiazol-4-ylmethyl,carboxymethyloxybenzyl, or cyclopropylmethyl; R⁴ is a hydrogen atom; orR³ and R⁴ may be taken together with an adjacent carbon to form a ringrepresented by the formula:

an optically active isomer, a pharmaceutically acceptable salt, or asolvate thereof.
 10. The compound according to claim 1, wherein R⁵ ishydroxy, an optically active isomer, a pharmaceutically acceptable salt,or a solvate thereof.
 11. A pharmaceutical composition containing thecompound as defined in claim 1 as an active ingredient.
 12. Apharmaceutical composition for inhibiting MMP-13 which contains thecompound as defined in claim 1 as an active ingredient.
 13. A method oftreating a disease resulting from, or associated with MMP-13 of amammal, comprising administering an amount for exhibiting thetherapeutic effect of the compound as defined in claim 1 to a mammalincluding a human.
 14. Use of the compound as defined in claim 1, forpreparing a medicament for treating a disease resulting from orassociated with MMP-13.